Alphabet Challenge
by campfiresongsong
Summary: As the title and rating implies, this is an alphabet challenge consisting of unrelated lemons. There will be more characters than what I have listed; and will also have a big variety in couplings. I will base most of my pairings and letter themes off of reviews, so if you have an idea; share it! J is for judicious
1. Anxiety

**A/N: Simply finding a good word to fit a theme around is difficult enough, so I think this will be a pretty tough challenge for me. I've only got ideas for 2 or 3 of the chapters so far, so feel free to suggest an idea and/or pairing; I'll try my hardest to fit it in! This chapter will be advanceshipping, but remember that this story will be a MIX of shippings and (mostly) unrelated stories. So if you simply don't like advanceshipping; skip this chapter and wait until one you like :)**

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**Anxiety**

It was 2:00 a.m. yet May still found herself awake on this calm and clear night. The Grand Festival was beginning this upcoming afternoon and she knew that falling asleep was going to be next to impossible. She was so nervous yet she so excited; this was the biggest event in her life! Just moving on past the preliminary round on such a stage would be a huge accomplishment for her.

She got up out of bed and walked out onto the balcony of their hotel room. Seeing the beautiful city skyline was soothing for her as she tried to push the upcoming contest out of her mind for the moment. She soaked in the view for several minutes before she found herself getting rather tired. She decided it would best to try and get some rest and crawled back into bed. Miraculously, she closed her eyes and sleep immediately overtook her.

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The next 10 hours had gone by in a blur for May. The contest was going to begin in a mere three hours and nerves were starting to set in for the young coordinator. The quartet was trying to decide what to get for lunch, but May didn't have an appetite. Her stomach was plenty full; full of butterflies that is.

Conversation had been going on in the background, but May hadn't paid it any attention before she decided to speak up. "You guys can pick a place yourselves. I don't feel like eating right now." The other three people in the room shared blank and understanding stares with each other because they knew how she must have been feeling.

"I think I'll stay back too," Ash said as he decided to be the first to speak up, "It wouldn't be right to leave May all alone right now." Brock nodded in agreement before nudging Max to the door so they could go and find a good place to eat. "We'll meet you guys at the contest hall." The breeder said before exiting the room.

As Ash looked sympathetically over to his younger friend, he remembered how he felt before his first match in the Indigo League. It was a very nerve-wrecking and stressful time. Because of his experience with the feeling, he knew what May needed; something to take her mind off of the contest.

"C'mon May, just stop thinking about it. We all know you'll be great so there is no need for you to get stressed out about it." He said in an attempt to help ease her mind. "I wish it were that easy." She responded glumly.

Ash walked over and sat down next to her on the bed. "I think I've got an idea of what we can do to help you out." He said with a look that May had never seen from him. Slightly confused, she looked up at him and asked "What's that?"

In a swift motion, Ash put his arm around her back and leaned in to bring their lips together. May's eyes shot open as she was completely caught off guard by Ash's unexpected move. He knew that this would not at all have been what she was expecting and he was unsure of how she would react. However, he did know that it would change what she was focused on.

May pulled back and gave Ash a stunned look while saying "What are you doing?" "Just go with it," he said, "Trust me." May was still extremely unsure about what to do, but this time when Ash pressed his lips against hers, she kissed back. She slowly found herself melting into the kiss as she pushed everything else to the back of her mind.

As the kissing got more passionate, May became more confident in the idea. She opened up her mouth and let Ash do some exploring. For someone who hadn't ever even had a girlfriend, Ash was a natural. He was extremely smooth and now had May under his spell.

He broke the kiss for a fraction of a second to get May's shirt over her head and off of her. May then returned the favor to the aspiring Pokémon master. Their fiery kiss continued as May reached her hand down and started to try and undo Ash's belt. She didn't take much time and she quickly tugged Ash's pants to the ground.

While she was doing this, Ash had gripped his hand on May's butt. He gave it a couple of squeezes before pulling her shorts off so they could join his. The two of them finally broke apart and locked eyes. A smile took over May's face as she reached for his boxers and ripped them off. Her mouth opened in surprise as she got a look at Ash's now freed erection. It certainly was bigger than she what she was expecting.

Ash smirked at the impressed girl in front of him. Not wanting to waste any time, he did the honors of lightly pushing May's mouth up against his beast. She took in a few inches of him and wrapped her tongue all around it. She started bobbing her head up and down, taking a little more every time she went down on him. Ash gave off repeated groans in admiration as the amateur sucked him off.

Ash now took a good look at May's rack. She had been blessed with hitting puberty early as her D cup breasts were poking their way out of the royal blue bra. He thought the bra had to be a push-up, but as he removed it to start to play around, they stayed up. Ash was amazed that breasts that size could manage could also be so firm!

As he started to fondle her huge boobs, May continued giving him fantastic treatment. She was now taking in a good 6 or 7 inches of him, and it was about all she could manage. She started gagging on his member as it went part of the way down her throat. She cupped his balls as she continued to work her tongue up and down on his shaft.

"Oh fuck, May" Ash let out. He gave both of her breasts a hard squeeze as she tried to hold on from cumming in her mouth. Knowing that would be an extremely difficult task, he brought May's head up. He groped her tits for one last time before letting go.

Ash laid back on his back and guided May into getting into a cowgirl position on top of him. Once she gave him the nod of approval, he entered inside of her slowly. She bit down on her tongue as she tried to keep from screaming out in pain. She sucked it up quickly though, and gave Ash the green light again.

He entered in about halfway, before retracting most of the way out, and slowly moving back in. He loved the outstanding feeling that he got as her tight pussy walls clamped down onto his hard penis. Ash let her dictate the pace, and she slowly let it increase as she became more comfortable.

"Oh yeah! Oh Yes! Yes! Ohhh yeahh!" May moaned out in pleasure as pace kept its gradual increase. Once the two of them had a little bit of a rhythm going, Ash reached back up and started to play with May's magnificent melons. He still had no clue how a girl her age could have boobs so big, but he loved it.

"Damn they're perfect" Ash grumbled out in fascination as he continued to squeeze away on his new found treasures. May smiled as Ash admired her chest. She knew that they were her best features and that they would be marveled at by many. She enjoyed having Ash fondle them, but it was nothing compared to what she was feeling thanks to his manhood.

"AHHH! Ahh! Ahh! Ahhh! AHHH! MHM! MHM! Oh god!" she let in pure pleasure as Ash started entering her fully and stretched her out to the max in the process.'He was so _big!_' she thought to herself as she soaked in every blissful second.

May's joy was taken to a whole new level as she finally released and had her first ever orgasm. "AHHHHH!" she let out a short and passionate scream to accompany to the powerful climax. Ash paused for a minute as he allowed for the beautiful brunette to collect herself.

Once she had returned back to Earth, Ash got off of the bed and pulled May off as well. He laid her back across a brown desk and had her hips at the edge. He crossed her legs while also setting them over his shoulders. He stayed standing and started to enter her once again.

This new position gave Ash more control and also allowed for deeper penetration. He wasted no time in taking advantage of either of those perks. He thrusted in deeper and with more vigor than before. "AHH! AHHHHH! AHH! OH! OHHHH! OHH YESSS!" May immediately started to squeal in pleasure.

As Ash continued pumping in and out of May, he really admired the wonderful view in front of him. May was a petite girl with a cute face and a nice smile. She had no pimples and had next to no fat. Her stomach was flat, but as already mentioned, her breasts were huge. He loved watching them bounce up and down as he rocked in and out of her.

Wanting to watch them bounce even more, Ash started raising the frequency of his entries. "OHHH! MHMMM! MHM! AHHHH! OHHHH MY GODD YESS!" May screamed out as the raven haired boy- wait no; man, kept pleasuring her.

"OH GOD ASH! OH YES! GIVE ME MORE! I NEED IT! HARDER! DEEPER!" she begged out. Now that he was given permission, Ash held nothing back. He entered in as far as he could before pulling out, and then sharply entered back in.

"OH MY FUCKING GOD! OHHHH! OHHHHH! AHHH!" May let out deafening screams while Ash penetrated to spots that she didn't think was possible. He was hitting her g-spot with every thrust, and she just couldn't get enough of it

Even though he wasn't as verbal about it, Ash was also in a state of ecstasy. Her pussy was so tight; even he was surprised that he could fit his whole member inside of her. Her walls clamped down on him so well, "Oh hell yeah" he muttered out.

"AHHHH! AHH! OHHHH MY GODD! OHHH YESSS! AHHHHHHHHH!" May let out an ear-splitting scream as she hit her second climax of the day. As her juices stormed out, May almost lost all sense of reality. She felt so empty yet so complete; it all just felt freaking fantastic.

Her inner walls clamped down even tighter with the expulsion of juices, causing Ash to very nearly lose control of his own cum. He managed to hold in all in though, and pulled himself out of the worn out girl. Knowing that she couldn't take another round, Ash turned his focus back to May's perfect pair of breasts.

He positioned his rod in-between them, and let May proceed to pleasure him. Feeling his cock get smothered by her cleavage was a major turn-on for him. It was sort of like a fantasy that he thought would never actually come true.

He could feel his release coming soon as he continued to play around with her tits. He rubbed his member against them while giving his final squeezes to them as well. He finally let out a deep groan as he shot his semen all over May's face and chest.

The two of them continued panting after the workout that they had just endured. May glanced over at the clock and her eyes widened as she realized that her report time was in a mere 30 minutes. She hurriedly threw clothes back on her and grabbed her poke balls before rushing towards the door.

Before she left, she looked back over at Ash and said "You were right." as a big smile took over her face. She then flew out the door and presumably toward the contest hall.

A smile also found its way onto Ash's face as he smugly thought, _She acts like that's a surprise_.

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**A/N: So I decided to try writing advance this time, next chapter will either be contest or poke. I have an idea for the story, but I'll wait to write it until I see which one you guys want me to write. If more people ask for contest, than so it shall be or vice versa. Please leave other shippings you'd like to see as well, I'm hoping to have a good variety throughout the story (keep in mind the rules I have on my profile though).**

**Thanks for reading!**


	2. Birthday

**A/N: The author's note at the end of this is pretty important, so make sure to check it out. It's a little lengthy, but it's a matter of life or death so you'd better take a look. Ok maybe not, but read it anyway! This chapter will be contestshipping and is unrelated to "The Rewards of Losing". It's my first story not set during Ash's travels. **

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**Birthday**

Drew set down his plate after he'd finished off the pasta that was served to him. "That was great May, thanks for fixing it. I'll get started on the dishes."

"No you won't," she stated sternly back as she shot out of her seat and to the sink, "you'll go and relax while _I_ do the dishes." Drew shrugged her off and started to run some hot water anyway.

"I'm serious!" she said while pushing him away from the stack of dirty dishes, "I'll do the dishes and when I'm done I'll give you your present." she finished with a small smile.

"You didn't have to get me anything," he began while gesturing out with his hand, "wasn't all this enough?" "NO! I had to get you a real present. Now get out of here!" she said, fed up with her boyfriend's persistence.

Drew finally gave up and left the room. After May and Ash headed their separate ways, May ended up running into Drew along the paths in Johto. The two of them ending up becoming traveling partners, and much to the amazement of many, a couple as well.

The two of them had just finished competing in the Cianwood City contest when May surprised Drew by telling him that she had renting a beach house for the two of them over the weekend. Drew hated having things done for him just because it was his birthday, but there wasn't much he could do about it.

About a half hour later, May emerged into the living room and plopped down a bag in front of Drew. "Happy Birthday!" she exclaimed. Drew eyed it for a second before saying "A Victoria's Secret bag?" He peeked inside and gave another confused look, "an empty Victoria's Secret bag?"

"Come upstairs if you want to see what was in there" said May as she gave him a suggestive wink. She scurried up the stairs and took a left turn into her bedroom. Drew gave the matter some thought, before lifting himself up and following her lead.

Upon entering the bedroom, Drew closed the door behind him. His girlfriend was now lying down on the bed, and she beckoned him over with her finger. She drew circles on his chest with the same finger before questioning him, "You want me to take these off?" in an obvious reference to her everyday clothes.

Drew slowly nodded his head in response. May removed her usual red bandana with haste before she began to unbutton her shirt. She purposefully took plenty of time undoing each one. Once she finally reached the end, she slipped her shirt off revealing her black lace bra.

"Oh my big breasts can barely fit inside this itty-bitty bra" she said teasingly while she rubbed her fingers along Drew's cheek, making sure to give him a good view of her breasts that were indeed poking out. She then proceeded on down to below her thighs. She continued performing her striptease, grasping the inside of her waistband but refusing to pull them down any.

She repeated a few similar movements before she spoke up again, "You want to take these off for me?" she asked as she crawled on top of him again. For the second time in a span of a couple minutes, the green-haired coordinator gave a small nod. He gripped both sides of her shorts before yanking them downwards and lifting the over her ankles.

As he did this, it uncovered exactly what May had been bought for him. She was wearing some black g-string underwear that matched with her bra. The sides that ran around her waist were about as thick as floss, and there were a pair of skimpy triangles that "covered" her front and back.

Drew's eyes widened as he got a good look at what laid in front of him. He had no idea how he had managed to hook such a fine looking girl, but he was extremely thankful at this point. Seeing that she was being checked out, May reached underneath her bra and began to play with herself. She gave a few rubs and squeezes to show him what he could have.

She then decided to end his pain, so she unhooked her bra in the back and let it join her accumulating pile of clothes. Drew immediately attacked his new friends with his mouth while letting the other one get worked on from his hand. May gave out a soft moan as Drew began playing with her C-cups.

Drew felt clothes being removed from him but he thought nothing of it because he was so focused on his new toys. He continued to squeeze one while licking and sucking on the other. After a minute or two of that, he switched. He kept this up for several minutes while getting some soft moans from May.

He eventually stopped once he realized that she had managed to completely undress him. May then gave him another saucy look before growling out "I've been a bad little girl. I need to be punished." Once he heard this Drew reached over and ripped off her skimpy underwear.

He pushed May down onto her back as he got his knees. He grasped her ankles, had her bend her knees and also brought up her lower torso off the bed so he could position himself at her entrance. Once he got lined up, he began to fire away.

The two of them had only had sex a couple of times, and each time had been more on the passionate side. Drew intended for this night to be a little bit different. He thrusted in his full length and established a quick pace right off the bat.

"OHHH! Ahh! Ahh!" May squealed out in surprise as she didn't expect for Drew to be so aggressive. It was what she asked for however, and it felt blissful. Drew continued to pump in and out of her while she consistently gave off shrills.

This angle gave Drew a wonderful view of the smoking hot brunette. She had just about every physical feature a guy looked for. Compelling eyes, a great rack, a slim stomach, long legs; she had the whole package.

He kept admiring her as began to pick the tempo up even more. May had been extremely horny and this new style of sex was satisfying for her. "OH YEAH! OH YES! Go harder! Go Faster! I need a full punishment!"

Drew complied with the screaming girl in front of him, giving her exactly what she wanted. He didn't exactly know why, but there was something incredibly enjoyable about making her scream like she was. He relished the aggressive role.

"OHHH! OH MY GOD! Here it comes! AHHHHHHHH!" May gave off her loudest scream yet as she also let out her first orgasm of the day. Her juices gushed in a forceful jet; it was the most powerful climax that she had ever given off.

Both of them knew that the night was far from over. Drew got straight up on his knees and he pulled May a little closer while throwing her feet over his shoulders. It wasn't much different than their previous position, but Drew would be able to penetrate a little bit deeper now.

"You're not done yet" Drew told a heavily panting May. He pushed himself back inside her following the statement, reaching to depths that hadn't been previously explored. Drew could no longer withhold from letting out deep groans of pleasure; his cock was getting squeezed tighter than it had ever been.

"Oh hell yeah. Take it. Ughh!" Drew let out moans that were covered up because May was much more vocal about her happiness. "OHHH! KEEP GOING! AHHHH! OH FUCK ME JUST LIKE THAT!" she yelled out as Drew pounded her most sensitive spots over and over.

As Drew continued to pound in and out of May, he could sense his clock ticking. He gritted his teeth so he could try to postpone his release as long as possible. Knowing that it wasn't possible to go on forever, he also started to use up his last reserve of energy. He used this energy to increase both the frequency and power of his thrusts. "OHHH! OHHHH! OHHH YESSS! OHHH! OH MY GOD!" May was giving off screams with even higher volumes to accompany Drew's new pace.

"AHHH! AH! AHHH! OH DREW!" May couldn't stop screaming in joy as she felt the finish coming for both of them. Drew bit his lip as he figured he had less than a minute. He refused to leave any energy left unused so he started to go all out.

"AHHHHHH! AHHHH! AHHH! OHHHHHH!" May let out painfully loud yells as she was now getting hammered. Drew was going harder reaching deeper than he ever had. It was a good thing for them that no one was walking around outside because the noise coming from the bedroom echoed out for quite a distance.

"OH YEAHH! THAT'S HOW TO PUNISH A BAD GIRL! OH YES! OHH! OH GOOD GOD!" May closed her eyes in bliss while she was getting absolutely drilled. When she had been planning out this night she hadn't thought it would get this intense. The sex was greatly exceeding the expectations that she had.

"AHHHH! AHH! AHHHHH! OHHH! OH! AHHHHHHHHHHH!" May gave off her final screams as she gave off a climax even stronger than the one she had earlier. Drew was unable to fend it off anymore, and he fired off his load just moments after May had done so herself.

Both of their intense orgasms lasted for a good ten or seconds; ten seconds that could only be described as heaven. After Drew finally quit shooting his semen inside of his girlfriend, he pulled out and silently prayed that the birth control pill was able to do its' job.

The two of them simply sat panting while they relished the unforgettable scene that they had just gone through. Once May managed to get her breathing back to normal, she curled up next to Drew and said "Happy birthday." Before pecking him on the cheek and proceeding to fall asleep.

"Best damn present I've ever had" Drew commented despite the fact that May was sleeping. Remembering how draining their intercourse was, he decided that it would be best to get some rest himself.

For the first time in weeks, Drew went to sleep with a smile as he replayed the events of the night again in his head.

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**A/N: I think that I've come up with an idea on how to decide what to write for each chapter. My idea is that I will leave four options at the end of each chapter (these four will come from requests from you guys or just my own ideas) and let you guys vote. I would make a poll for each one, but I will also count results in the reviews (so technically you could vote twice!). I will close each pole on Sunday night when I upload the latest chapter. You get it? Let me try an example…**

**Today is Sunday, January 26****th**** so you have until Sunday, February 2cd to vote on the options I will leave. On February 2cd, I will upload my chapter "C" and close down the voting for chapter "D". Throughout the week, I will work on writing chapter "D" while giving you guys time to vote on what options I gave for chapter "E". The cycle just keeps repeating until I'm done. Each chapter will be approximately 2k in length.**

**I like this idea because it requires me to upload weekly, and incorporates both my ideas as well as your guys. Hopefully I did a good enough job explaining it. If you have some tweaks that you would like to see in the model, let me know! Without further ado, here are the optional pairings for chapter "D".**

**A. Pearlshipping (AshXDawn)**

**B. Trickyshipping (LanceXLyra)**

**C. Commandshipping (GiovanniXDomino)**

**D. Lustshipping? Might be wrong name but (BrockXJoy) Might also throw in Officer Jenny and make it a threesome**

**I know that I had gotten requests for at least two of those in the past, so I put them up for vote. Remember, there is a poll on my profile where you can vote but if you simply leave your answer in the reviews, I'll add it to the poll totals. **

**I've had multiple requests for amourshipping; I'm just waiting to see a few episodes with Serena before I write about her. I've never seen one so I wouldn't feel comfortable about it just yet.**

**Thanks for reading!**


	3. Curiosity

**A/N: I'm terribly sorry that I had to repost but I simply couldn't find time to write a new chapter. I had multiple papers, projects, meetings and then there's always basketball. But you don't want excuses, so I'll just say sorry again and shut up. Poll results and new poll will be at the bottom A/N.**

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Misty stared at Ash as he sat polishing his latest gym badge. Just the other day he had managed to defeat Erika and earn his Rainbow Badge. Misty shook her head watching him hum horribly off tune to some song while wearing his stupid grin of his.

"Four down and four to go!" exclaimed Ash, his smile still as apparent as ever. Misty said nothing, but continued with her ponderous look. "I can't wait to get to Fuchsia City and earn my Soul Badge!" continued Ash.

"I happen to know the gym leader of Fuchsia City; his name is Koga. He is by no means a pushover Ash, you'll have to train hard before you rush into town and demand a battle." said Brock as he looked up from the stew that he was making the trio for lunch.

"Yeah, yeah," Ash responded as he brushed off his friend's advice "You know that I'll train plenty hard. I always do. But for now, when's lunch going to be ready?" questioned Ash.

Brock chose not answer at first, but rolled his eyes at the young trainer's eagerness. "Soon enough Ash, just try to stay patient."

"My God Ash do you care about anything other than Pokémon and food?" said Misty as she finally decided to enter the conversation.

Ash could think of no retort so instead chose to playfully stick his tongue out at his red headed companion. Misty gave a little snort and another shake of her head.

As Ash went over to talk to Brock (more like pester she thought), Misty drifted off into thought. What did Ash care about? Obviously Pokémon. Whenever he wasn't complaining of an empty stomach or busy filling his stomach with food, his mind was on Pokémon. Whether it be training, discussing battle tactics or re-living his past battles, Ash was always talking about Pokémon. Shouldn't guys Ash's age be concerned about things like sports, music and girls? As Misty asked herself this question in her head, her answer brought forth another strange question.

Was Ash gay?

It seemed silly, but Misty could think of no way to positively answer the question negatively. The only time he had ever seemed to be interested in a girl was when he met Giselle, but Misty couldn't help but think he was simply pretending to be attracted to her because Brock was. It would be a shame if he was gay she thought, he was a pretty attractive guy. A little smile crept on her face as she thought about the day at the beach when she had seen him shirtless. She wasn't going to lie to herself, she had a small crush on him. With her curiosity peaked, she now wanted to figure out a way to find out the answer.

"Man, I sure wish I could cook like you Brock. That was great!" Ash remarked later that night after gobbling down yet another delicious meal put together by the Pokémon breeder.

"Oh that was nothing." responded Brock with a small smile "It sure is getting cold, we should probably build a fire. How about we split up and go get some firewood?"

"Oh I don't really want to go out by myself though," started Misty as a plan slowly started coming to mind "How about Ash and I go out together?"

Brock seemed to sense that something was slightly out of the ordinary, but didn't bring it up. "Alright then, try to get back here as quickly as possible though you guys." Brock instructed before walking off into the woods by himself.

_Perfect_, Misty thought. Now how exactly was she going to pull this off?

"Way to go Ash, now we're lost!" Even though she seemed to be angry with her idiotic traveling companion, she wasn't really. This situation could be put to her advantage.

"Well you're the one who chose to come out here and follow me in the first place!" retorted Ash, with a small hint of venom in his voice.

"You're right Ash, I did."

Slightly confused at Misty's agreement, Ash paused before muttering, "Yeah… well of course I am."

"Do you want to know why I came out here with you?" Misty questioned as she leaned up against a redwood tree.

"Umm... to get firewood?"

"No. I'm curious about something. Come here."

Ash hesitated, what the heck was going on? She wasn't out here to get firewood, but rather to question him? What did she want? These questions raced through Ash's mind as he slowly trudged over towards Misty.

This wasn't going down quite the way Misty had planned. Then again, she really didn't have a plan. She was improvising everything. During her thoughts and visions on what might go down tonight, she had not seen herself doing what she was about to do. But she didn't think any. She had started letting her body think for her instead. She quickly grabbed Ash by the waist, and pulled his lips into hers.

Ash was too stunned to make any movement. He didn't kiss back, nor did he pull away. Misty didn't let this faze her however; she just kept letting her hormones make her decisions for her. She figured she hadn't struck out yet, so she decided to swing for the fences again. She slowly traced Ash's lips with her tongue before forcing her way inside.

At this point, Ash's thought process finally started to kick in. Misty was kissing him. Misty. The girl who constantly complained and pointed out his faults to him, was now kissing him. It did not matter whether or not he truly liked Misty at this point. His hormones had kicked in too. He quickly started to reciprocate the kiss.

Misty gave out a small moan, both out of relief and pleasure. She enjoyed the spontaneous moment for a while before finally pulling away. Before Ash could even stutter his way into a sentence, Misty put her finger over his lips. She gave a seducing smile before sliding Ash's vest off of him. She followed that by removing his hat and shirt. Then she took her sweet time fumbling with his belt, she wanted to tease the boy a little bit first. Once it was removed, she didn't even bother to ask permission before taking his jeans and boxers off in one quick move.

If Ash was actually thinking at this moment, he might have stopped her. But he couldn't think right now, during this experience that he had never dreamed of experiencing. He just let Misty do whatever she wanted.

Misty didn't quite know what to do; she was as new to this as Ash was. His cock was erect and at least half a foot long. Was that big? Was that small? It seemed big to her anyway. She finally slid her mouth over it, and started to use her tongue.

Ash was in a state of euphoria. Nothing he'd ever felt even come close to what he was feeling at this moment. Misty continued to bob her head up and down on his shaft, bringing multiple soft groans from Ash. This felt too good. It was unbelievable. And he wanted more. He put his hand on the back of Misty's head and pushed.

Misty gagged as she tried to fit his whole member inside her mouth. It was extremely uncomfortable at first, but she figured that you had to practice if you wanted to get comfortable with this. She would occasionally take her mouth off and stroke him a few times before sucking him off some more. She tried licking the tip, and could tell that this too was pleasurable, yet teasing too. Soon, as she started to get the hang of loosening up and using her throat muscles, she could tell it was extremely pleasing Ash.

And as wonderful as it did feel to Ash, he stopped her. He couldn't wait anymore. Misty raised her arms and let him slide her shirt up and over her. She then unclipped her bra, and let her perky nipples out. Her breasts were on the small side, but they fit her body nicely. Ash quickly yanked her shorts off, and her panties followed soon after. Her legs were long and toned dramatically due to all the swimming that she did. As Ash's eyes traveled up her legs, he noticed her hairless clit and her firm butt. She looked pretty sexy.

"This is going to hurt." Ash warned.

"I know, but I'm ready." responded Misty, her tone of voice proving that she was indeed ready.

Ash wasted no time in responding to the green light, and slowly inserted his cock into her pussy and broke through her wall. Misty's mouth stretched into a big O as she tried to keep from screaming right into Ash's ear. The pain was excruciating, and she thought she might cry. Just when it came to the point that it was almost unbearable, the pain started to subside. After a few heavy breaths, she was ready.

"Go ahead." She instructed

Ash went in as far as he could before withdrawing back out, and inserting himself back in slowly. He increased his speed gradually as both their comfort levels started to rise. The faster he went, the greater the feeling. Their timing with each other began to sync up and soon Misty began releasing constant moans.

"Harder," she commanded as she positioned herself so that the tree could provide support for her.

Ash quickly complied. "Don't hold back anything." Misty managed to get out between squeals of enjoyment.

His smile intensified with her latest order, and once again he listened. He rammed her with all the force he could muster up. Misty now knew she was on the verge of her climax. "I'm almost there Ash," Misty warned "AHHHHH! THIS FEELS SO GOOD!" She screamed as she released her juices. It was an incredible feeling, and she wanted to feel it again. "Don't stop now Ash! I want this to last for a while." she commanded.

Ash didn't need to be told however, he had no intentions whatsoever of stopping. His thrusts kept coming, each one seemingly more powerful. "OH OH OH OHHH just like that, just like that, oh YES!" Misty screamed as her rough defloration continued. The bark was pressing into her breasts with each fierce movement that she was making, which only multiplied the bliss. She no longer tried to keep her voice down. She was screaming at the top of her lungs as she hit an orgasm, her second.

"OH GOD ASH, KEEP GOING, PLEASE KEEP GOING! OHH YESSS! PUNISH ME LIKE THE SLUT I AM!"

Ash continued with his torrent pace for as long as he could, but he knew he couldn't last forever. Misty had already released a couple of times and he knew he was getting close. He knew that he only had seconds left, so he made them count. He seemed to get an extra adrenaline kick or something, because he managed to multiply his force to even greater levels. Misty's screams were now so loud that they were inaudible to him in a way.

He didn't want to release inside of her so he quickly pulled out. Misty knew that it was now up to her to finish the job. She quickly grabbed his penis and started stroking it again. She opened up her mouth and swallowed it again, her tongue working wonders. Ash knew that this second blowjob would finish it him in a hurry. "Here it comes, Mist!" he shouted before releasing his full load inside of her mouth.

She initially tried to swallow it all, but there was just so much that she couldn't get it down. She started to pull her head back but Ash put his hand on the back of her head and forced her all the way back down. He wanted for this to end his way. "Swallow." he simply commanded. Misty gagged as she tried to fit his somehow still erect cock and his full load of semen in her throat. After several seconds, she finally managed to swallow it all. Ash released his hand and let her come up.

Misty took some deep breaths, while looking up at Ash. They both didn't quite know what to say. They didn't know what had overcome them in that special moment that they had just shared. Misty decided to break the small awkward silence, "We should get back to camp. Brock's probably worried about us." Ash just nodded his head, they could discuss this later.

After walking around for a few minutes, they managed to find their camp again. Brock was sitting on the ground, by the fire that he had built while his companions were out doing their own thing. "What the heck happened to you guys? What took so long?!" Brock asked to his friends with blank looking faces.

"Umm... well we got lost. Really lost." Misty lied unconvincingly. She could tell that he didn't believe her, as he stared her down trying to get a read on her.

Wanting to get out of this situation, Ash quickly announced that he wanted to go to bed early, and crawled into the tent. Misty inwardly cursed him for leaving her alone with Brock. Once he was out of sight, Brock cracked a smile.

Misty looked at him, obviously confused. "Wh-what are you smiling at?"

"Well you see, I got concerned about you guys after you didn't come back so I went out looking for you. Once I got in about a 200 yard radius, your screaming did the rest." Brock said with a smirk.

Misty's whole face went red as she comprehended what he said. He saw them! Or at least heard them anyway. She was so embarrassed that she couldn't think of anything to say. "..."

Brock let go of a short chuckle before adding, "You know, you still could have gotten some firewood on your way back. That is what you were supposed to be getting you know." Brock enjoyed taking in the girl's uncomfortable look for a few more seconds, before deciding that she had suffered enough. "I'll pretend it never happened. Goodnight." he finished before going over to the tent Ash had entered not too long before.

Misty was still shell-shocked. She would never live this down.

"I really need to control my curiosity..."

* * *

**A/N: Tied for last place with just one vote apiece was Commandshipping and Trickyshipping. Pearlshipping came in second with 8 votes. Lustshipping came on top with 9 votes. So I'll be writing lustshipping for the next chapter, and something tells me pearlshipping will win this time based off the big support it got last time. I was very happy with the amount of people who participated last vote, so let's get that many votes again!**

**The options for chapter "E" are the following: **

**A. Pearlshipping (Ash and Dawn)****B. Gymshipping (Brock and Misty)****C. Brunettshipping (Gary and May)****D. Wishfulshipping (Cilan and Iris)**

**So answer in the poll question on my profile, put your answer in the reviews, or both!**

**Thanks for reading!**


	4. Dream

**A/N: Just in case any of you might be offended, this is a threesome (maleXfemaleXfemale). This takes place back in Kanto so Joy and Jenny look like they did back then. That's about all you need to know; so I'll check back in at the end of the chapter!**

* * *

**Dream**

There had been a break-in at the Pokémon center that Brock and his companions were staying at. Someone (presumably Team Rocket) had stolen some very valuable Pokémon medicine. Officer Jenny was currently on the site and discussing the matter with Nurse Joy.

Brock looked at the ladies in admiration. He racked through his mind, trying to come up with a good pick-up line for the two of them. Which one should he go for? Nurse Joy was so beautiful, but so was Officer Jenny. Did he have to choose?

Finally settling upon the perfect lines, Brock approached the girls. "Nurse Joy, I think I need a paralyze heal!" "Why?" She asked Brock, who was basically a stranger to her. "Because you're stunning." Brock finished with a dazzling smile.

Joy blushed a little before stammering out a thank you. He then turned to Jenny and said "And as for you Officer Jenny; you remind me of a Deoxys, because you're out of this world!" Jenny blushed a little herself and let out a giggle.

"Well you can't hit on both of us, that's just not right," Jenny began "You have to pick one." Brock thought momentarily about what to do; should he go for Jenny or Joy? Were they just messing with him or were they actually flattered? Either way, it was worth a shot.

"I simply can't choose between two women as beautiful as you, though!" Jenny gave a laugh before asking the strange man, "What's your name, cutie?"

"My name is Brock, but if I were a Pokémon I think that I'd be an Erectabuzz." He replied before shutting both his mouth and eyes in disgust with himself. Why the hell did he have to make a sexual joke? Misty wasn't here to stop him from picking up a girl, and he ruined his chance by saying something so immature and stupid.

Both Joy and Jenny had shocked faces from hearing what he had said, but to Brock's surprise, neither seemed to be appalled. Instead, they shared a knowing glance, and Jenny then looked back at Brock. "If that's true, then why don't you show us?" She said with a suggestive smile.

Brock found himself speechless after hearing those words. He thought for sure that he'd earned a slap for being so forward, but instead they seemed to be going along with it. He wasn't able to put together a sentence, but his facial expressions showed his emotions better than words could anyway.

"It's been a long time since either of us has had sex. I think we've both got a lot of pent up sexual tension waiting to get out." Jenny said as she continued to speak for the two of them.

Brock thought his jaw might hit the floor. Jenny took off her police belt as well as her hat while Nurse Joy removed her hat and her white blouse. "Why don't we go ahead and start the show, honey?" Jenny asked Joy.

The two of them locked lips and quickly started to make out. Brock must have thought that someone was messing with the thermostat because it was getting extremely hot. The two women's hands were flying everywhere and removing all clothes possible.

Brock simply had to take off his pants at this point to help ease the pain of his throbbing erection. He undressed himself while Joy and Jenny continued with their French-kissing. Their tongues fought a war while they let out passionate moans to each other.

Before Brock could start to jack off to them, however, they pulled away from each other. Joy had been stripped down to her pink one-piece. The triangle that covered her up front rose up and gave her stomach a little coverage and were protecting her D cups from spilling out.

Jenny was donning a two piece set of blue underwear that matched the color of her police hat. Her huge breasts were also threatening to pop out. Neither of their outfits left much to the imagination, but that was still too much for Brock.

The two girls did the honors for each other, each exposing the other fully. Both were fully shaven and their breast sizes were nearly identical. Not only were they huge, but almost more importantly, they were firm. Age hadn't had an effect on them yet; there was no sag.

Joy hopped up onto the counter that she normally stood behind at work. She dropped her head off upside-down on one end and left her clit at the other end. Brock got in front of her head and let her mouth cover his member. Jenny positioned herself on the other end and started to eat her out.

Joy took in about half of Brock, wrapping her tongue all round him. Jenny knew exactly what she was doing on the other end, and drew moans that were stifled due to the fact that Joy had her mouth full. Brock closed his eyes as he received a blowjob that he honestly never thought that he would ever get.

Brock decided that this was the perfect and probably only opportunity he had to fill one of his fantasies, so he started to face fuck Nurse Joy. Brock used his hands to move her head in a way that it was in sync with his hips. He would bring her head down while he thrusted forward so he could reach far inside her mouth. Joy gave some good gag-reflex action as Brock continued to ram his cock down her throat.

At the same time, Jenny was making a very horny Joy even more wet with the work of her tongue. She used her fingers to spread Joy more open and stuck her tongue in the opening. Joy and Jenny had done this before and Jenny knew just what to do to please her.

Joy was experiencing such pleasure that she knew that she was on the verge of her climax, but before she released anything, she decided to change things up. She had Brock lay down on his back on the floor. She sat down on his fully elongated erection while also leading Jenny to sit on his face.

Brock started to eat out Jenny while letting Joy ride on his member. The girls were facing each other which allowed for Jenny to lean over and play with Joy. She started to use her tongue again, but this time it was in a new location. She also started to receive the very same treatment that she had just given to her pink-haired friend.

Joy let out a long moan as a wave of fantastic feelings took over her. It had been months, wait no, YEARS, since she had had a man inside her. The feeling was almost new to her since it had been so long, and she planned to make the most of this rare occasion.

Brock was enjoying the moment every bit as much as the sexually deprived girls were. Since Joy hadn't been penetrated in so long, she was still very tight. She was making it very slow and sensual so that both of them could soak in the feelings. Brock was getting his cock squeezed tight and Joy was getting filled plenty despite Brock's slight lack in size.

The girls were both letting out some soft moans filled with pleasure. "Ahhhh. Ohhh yess!" They had all forgotten about the robbery that brought them together at this point. This took a higher priority in their minds.

Brock used his tongue to the best of his ability while fully enjoying what he was getting down below. Jenny was now using one hand to stimulate Joy's pussy even more, and she used the other to give attention to Joy's mounds. She used some techniques that she hoped would get her partner off soon; she wanted her turn with Brock.

Luckily for her, Joy was once again on the verge of her climax. She was now bouncing at a slightly faster pace, and it was possibly the greatest feeling she'd had in the past few years. "Oh my god! Uhh! AHHH YESS!" She finally orgasmed with Brock still inside of her. Brock, however, managed to withhold his climax.

After letting Nurse Joy regain her sense of reality, Officer Jenny took her spot on top of Brock's rock hard cock. She, however, laid down and faced the other way. Joy then sat on Brock's and faced the same direction as Officer Jenny.

Jenny immediately let out a long moan now that she was able to experience the same feelings that Joy had. It had been equally as long for her since she had been entered, so she was just as wonderfully tight. "AH!" she let out in surprise and enjoyment as Joy leaned forward and started to give her a rimjob.

They had never experimented with this, but it felt great for Jenny. She was getting the penetration that she so desperately craved while also having her anus licked out. For Nurse Joy, it wasn't as disgusting as it might sound to some. It was very different from anything else, but it wasn't vile.

Brock was able to stay in his heaven. His penis was being tightly squeezed once again, and now he was able to eat out Joy. Not only that, but his chest aligned perfectly with Joy's so that her fantastic breasts pressed down into him.

Jenny took a slightly faster pace than Joy had; she wanted satisfaction and she wanted it as soon as possible. What she was feeling was far more superior than satisfactory though. The rimjob was something new that felt great, but it simply couldn't compare to having a man fill her up for the first time in so long.

Joy started to rotate every minute or so; she would move her tongue from one hole to the other. She wanted for her friend to be able to have a powerful climax. She, herself, was having to use a little bit of willpower to keep Brock's mouth from having her release again.

Brock was still in his state of pure bliss. His two favorite women were giving him the best time of his life. He was now timing his upwards thrusts with Jenny's bounces. He could tell that she was getting close to finishing because of the sounds she was making.

"OH! Oh my god! YES! It's been too damn long!" she let out joyfully. She decided that her statement held a lot of truth and it was time to fix it. After a few more pushes, she released her juices with a final yelp. "OHHH HELL YEAH!"

Brock knew that this night wasn't going to end until he finally gave out, so he got ready for another round. Officer Jenny put a devious look on her face before walking back to her police belt. She came back with a pair of handcuffs and gave a dirty look to Nurse Joy.

She slapped them onto her, before shoving her into the counter that she had laid on earlier. "You have the right to remain silent. Anything you say can and will be used against you in the court of law." She said while Brock set up behind the bent over Nurse Joy.

He entered behind the "delinquent" and immediately started to pump in and out. Joy wasn't exactly sure how she was supposed to remain silent throughout this. Brock didn't wait too long before picking up the pace. Joy simply couldn't hold it in anymore; "AHHH!" she let out.

Having stripped everything else off her belt; Officer Jenny knew what she could use it for now. She gave a light whip to Joy, "You have the right to remain silent!" She said in a firm voice. Joy now bit her lip in the hopes that it would help her to cease from making any noise.

Brock now had a smirk on his face and he started to become a little rougher. Each thrust was a little harder than the one preceding it. "OHHH! OH!" Joy had to let out another squeal. Jenny again cracked the whip; this time she hit her twice. "I said you have the right to remain silent!"

Brock was fully enjoying the show in front of him, and decided that he would step it up another notch. He started to go as fast as he could make himself go in an attempt to make Joy scream. Joy was panting heavily, but there was nothing she could do to hold in her yells now.

"AHHHH! OHHH! OHH!" She screamed out. Jenny took no time to bring the whip back out. She started to hit her a little harder, not hard enough to seriously harm her of course, but enough to enforce the law. The whips weren't enough to silence her anymore though.

"OHHH! MHM! MHM! AHHH!" She continued to scream because of the pounding that she was being disciplined with. Because of her constant screams, Jenny made the whipping continuous as well. She had been placing them on her back, but now moved down to her ass.

This only raised the volume of Nurse Joy's screams, "OHHH! OHHH! AHHHH! AHHHH!" she screeched out. "You. Have. The. Right. To. Remain. Silent." Jenny said while whipping Joy once with every word that she said.

Brock just kept pummeling Joy throughout all of this. Joy almost seemed like she was crying at this point, "AHHH! UHHH! MHM! UHH! MHM! MHM!" she didn't even bother to try and remain mute any longer. Jenny just kept giving her lashes, changing cheeks after every couple.

Joy let a huge orgasm at this point, but Brock just kept pumping away. "OH DEAR GOD! OHHHH!" Joy sunk her face down onto the counter to try and muffle her screams some. Brock was having none of that. He reached for her circular strands of hair tied together in the back and he pulled her back up, forcing her to arch her back in the process.

This allowed for Brock to get even deeper and at this point Nurse Joy's screams were practically ear-piercing, "AHHHHHHH! AHHHHHHHH! AHHHHHH!" Officer Jenny had whipped both of her cheeks red and she decided it might be best to quit that for now. She instead tied It through the loops in her hair so that she could yank her up if need be.

She also reached for her bouncing breasts and started to play harshly with them. She gave them a few pinches and squeezes while reminding her that, "You have the right to remain silent!" With that statement, she pulled roughly up and yanked Joy's whole upper body up.

Jenny somehow felt sorry and jealous of her pink-haired friend at the same time. She made sure not to show either of these emotions though. She continued to give harsh squeezes on her boobs while Brock gave her everything he had on the other end.

What he lacked in size, he made up for in skill. He knew how to use what he was given, and he was really giving it to Joy now. She had managed to stay quiet for a few moments, but it was all simply too much. "AHHHHH! I CAN'T DO IT! OHHHHHHH!" She let out in a painfully loud manner.

Jenny now reached back with her bare hands and started to spank the poor lady. "You will remain silent!" She commanded while giving her some rough slaps. This once again got Joy to hush up, but Jenny didn't care. She slapped her regardless; simply to remind her who was in charge.

She'd already orgasmed twice on the night, but Joy knew that another was coming. "AHHH!" She let out a squeal and put her head back down. Jenny responded by harshly jerking her head back up and slapping her even more.

Joy felt so helpless. He hands were cuffed behind her back and her upper body was being forced into the air. It may have been a little painful, but it was extremely erotic and she was moments away from climaxing.

"OHHHHH! AHHHHH!" Joy had to start screaming again. Jenny slapped her with even more vigor now, "That's quite enough!" She stated. Brock didn't let up any; he just kept pounding the innocent girl.

"OHHHHHHHHHHHHH! AHHHHHHHHHHHHHHHH!" Joy let out a final scream as she gave off a monstrous orgasm that made her lose control of her body. Brock and Jenny stopped at this point; their job was done.

Joy felt weak from her amazing climax, but she kept consciousness. "You aren't done yet." Jenny told the poor, worn-out Nurse Joy. She shoved Joy's mouth over Brock's manhood and said to her, "You have to finish what you started."

Jenny herself took the pleasure of sucking on Brock's sack whilst forcing Joy to bob her head up and down Brock's shaft. He let out long groans in approval as the two girls gave him wonderful oral treatment. He reached behind Joy's head and joined Jenny in forcing her down.

He forced her to take his full length and wouldn't let her back up. She wrapped her tongue around him and covered every inch of him that she could. Part of him went down into her throat, and she managed to keep from choking on it.

Brock reverted back to what he did earlier in the night by beginning to face-fuck her again. This time, he had the added pleasure of Jenny sucking his balls. He continued to jab his cock inside of Nurse Joy, forcing his way down her throat.

Unfortunately for Brock, his miracle run was coming to a close. He had no idea how he had kept from releasing from so long, but he was getting extremely close now. He gave a few more quick pumps in and out of Joy's mouth before pulling out and lifting Jenny's head as well.

He shot his load all over the two ladies. He showered them as jet after jet of cum flew out of his penis. Once he finally finished releasing his semen, Joy and Jenny were covered in it. It was all over both of the girl's faces and it dribbled down onto their chests as well.

The girls winked at him simultaneously and Brock made sure to take a mental photograph of the extremely hot image in front of him.

* * *

Brock felt a pillow strike him in the face and he woke up in a jolt. He looked around and quickly gathered that Misty was the culprit. He gave her a look that asked "Why?"

Misty shook her head and said, "You wouldn't stop talking in your sleep for some reason so I had to wake you up."

Brock's eyes widened in realization before mumbling softly, "That was one damn good dream."

* * *

**A/N: Poor Brock XD. Well that was longer and more intense than I'd planned. Hope I didn't go to far. I actually like it, and if this gets good reviews, then I think I will make more threesomes and moresomes.**

**Pearlshipping got 8 votes and nothing else even got a vote. So I'll be writing pearlshipping. The options for next chapter are as follows:**

**A. Kissshipping (Ash and Melody) B. Egoshipping (Gary and Misty) C. Ikarashipping (Dawn and Paul) D. Amourshipping (Ash and Serena)**


	5. Exuberance

**A/N: This chapter will be pearlshipping. Poll results and new poll at the bottom. Think I might start to reply to reviews in the A/N if you guys want. Just as a broad response, thanks to everyone who read, and an extra thanks to those who reviewed and/or voted. Oh and I realize that the timeline for this story doesn't match up with the anime, but oh well.**

**Exuberance**

The smoke cleared, revealing a beat-up Pikachu that was miraculously still on its feet and a Dragonite that was out cold on the ground. The crowd exploded into cheers for Ash as he had now moved into the finals of the Sinnoh League. Ash pumped his fist and sprinted to his trusty party to celebrate their huge win.

* * *

The hours proceeding Ash's epic battle flew by for the Pallet-town native. It was now past midnight and he was back at the hotel that he, Dawn, and Brock were staying at. The three of them had gotten separate rooms because each room only had one bed. There was a knock at the door and Ash assumed that it had to be one of his traveling companions.

He opened the door and found Dawn standing outside with a smile. Ash immediately let her in. "Guess you aren't ready for bed yet either?" he asked, starting the conversation. "I'm still up for a little more celebration," Dawn started with a small giggle, "this is all just so exciting!"

Dawn had managed to win the Grand Festival the day before, and now Ash was one round away from winning the Sinnoh League. It was safe to say that this was easily the highest high that either of the two young trainers had experienced before.

"Yeah I know. I don't think I'll be able to sleep; I've still got so much energy in my system." Ash replied. He certainly wasn't lying; this was the first time that he had sat down since his match ended. He had never been this amped up in his life.

The two were just sitting on the end of the bed, enjoying each other's company despite the silence that had arisen. Dawn didn't exactly know what came into her head at this point, or why she did what she was about to do.

She leaned over and gave Ash a quick peck on the lips. "Congratulations" she whispered out. Ash froze, he didn't know how to react. Should he take it at face-value, a simple congrats? Or did it mean a lot more than that?

Without wasting too much time, Ash decided to lean over and give a peck back to her. "Congratulations to you too" he whispered back. Light brown eyes locked with a pair of vibrant blue eyes in the ensuing moments. Their pupils seemed to be able to communicate better than their mouths right now.

Suddenly, their eyes closed and their mouths took over the task of communicating once more. Instead of speaking, however, they did it by enjoying a lengthier connection of the lips. Dawn wrapped her arms around Ash's neck and deepened the kiss.

After running out of breath, Ash had to pull away. Shocked by his own actions, Ash momentarily froze again. He snapped out of his little trance as Dawn began to speak again. "Why don't we go ahead and get rid of these clothes?" She asked with a little purr.

Ash managed to give a small nod as he began to wrap his head around the magnitude of this moment. Ash slipped his shirt over his head while Dawn brought his pants to the ground. She got on her knees and looked up with a smile.

Seeing that he wasn't going to back out, Dawn went ahead and pulled his red boxers down as well. His somewhat aroused member popped free causing Dawn's eyes to widen. She was by all means a virgin, and she honestly wasn't positive how to go about this. It was too late to back out now, however, so she brushed off her second guesses and chose to get on with it.

She opened up her mouth and then went down on him. She only took in a couple inches to start; she was only a beginner after all. She whirled her tongue around, trying to give equal attention to every part of him. After gaining some comfort, she began to bob her head up and down.

Ash's groans told her that she was doing the job right, but the fact that his rod hardened up and extended out some more solidified the fact even further. The more her confidence rose, the more that she tried to take in. She found herself to be able to take in most of him, about six inches, but she gagged if she attempted to go down any further.

She continued to bob her head up and down, all while keeping her tongue in constant movement. Ash continued to groan and grunt her name out as he received his first blowjob. The feeling was so wonderful and so unique; it simply had no comparison. He closed his eyes briefly, just enjoying the unbelievable moment.

He now started to act solely on instinct, albeit that is what he does most of the time anyway. He pushed on the back of Dawn's head, forcing her to choke on him. The sound of her gagging added an extra enjoyable element. He let her go to breathe for a while, but Dawn got the message.

She went all the way down on her own this time, even though she couldn't fit it in. She knew that it wouldn't be long before this would cause Ash to lose control. Confirming her beliefs, Ash began to groan louder and a little more frequently.

Unable to take it anymore, Ash put both his hands behind Dawn's head and thrusted forward for the first and last time. He orgasmed with his dick still filling her mouth and sticking part of the way down her throat. He immediately retracted in order to give Dawn some air.

She managed to swallow everything that he had shot inside of her. Surprisingly, Ash was still completely erect, and they both knew that this meant there was more action to come. She stood up and walked right over to the naked Ash and whispered huskily into his ear, "You know, I'm not wearing any underwear."

She was still wearing her cheerleading outfit from earlier, and evidently that was all she had on. Ash looked at her and matched her naughty smile with one of his own. He pushed her onto the bed, and pushed her legs so that they were separated and in the air. He lifted up the bottom flaps of her outfit in order to expose her vagina.

The bed happened to be at such a height that Ash only had to give a slight bend in order to meet her. He stopped right at her entrance and made sure that he did, indeed, have the approval to keep going. "Put it all the way in there! I'm ready!" She said with complete confidence.

Ash entered inside her slowly, and upon reaching her protective barrier, he gave one quick, hard thrust in order to break it down. Dawn picked a pillow up and used it to cover her screams. Why must you endure pain like that before you can have sex? The agonizing pain subsided after a short little while, and Dawn nodded again at Ash, now giving him permission to continue.

He began to push in and out at a very slow pace. The feeling that Ash got when Dawn's virgin walls gripped down tightly onto him wasn't surpassed by anything. It put the feelings he got from the blowjob to shame.

"Good god you're tight." Ash commented in his state of felicity. He began to inch the pace forward, but he only took baby steps to make sure that they both stayed comfortable. He didn't want to rush things; there was no reason not to extend these jubilant moments for as long as possible.

Dawn was letting out long, soft moans as Ash penetrated her. She didn't have anybody to compare him to, but from her experiences trying to fit him in her mouth and now down below, she was pretty sure that he was on the big side. He was certainly a tight fit, heck, in her mind, a perfect fit.

She could feel that he was increasing the pace some, but she really wanted to feel it now. "Go faster! Harder too!" She begged to the hopefully soon-to-be Sinnoh Champion. He said nothing in response but rather let his actions do the talking.

He complied with her, letting the pace swell and giving much harder thrusts. He smiled as he looked down at the bluenette. She was stunning; she looked good enough to be cheer-captain. Fittingly, she was wearing her cheerleading outfit, letting Ash pretend that she was, indeed, a cheerleader. There's just something about guys that makes them attracted to the thought of screwing a cheerleader.

"OH GOD! Yes! So good!" Dawn was becoming more passionate in her dialogue now. Ash was reaching deep inside her, and stretching out her walls about as far as they could currently go. "Give it to me! Fuck me harder!" She commanded out rather helplessly for a command.

Ash hardly let her finish the sentence before he went in accordance with her. He packed plenty of power into each thrust now, making her scream even more. The sight of the screaming cheerleader was an extremely hot image to Ash, and helped him find more strength.

"OHHH! AHHHH YESSSS! Just like that! AHH!" Dawn squealed out as she crept closer to a climax. Ash seemed to know exactly where her g-spot was because he repeatedly smashed into it with tenacity. She was having a very tough time keeping the noise level down, but she honestly didn't care too much right now.

"AHHHH! OHH! AHHHHH!" Dawn let off her loudest scream yet as she had her first ever orgasm. Hers' lasted slightly longer than the one that Ash had earlier. She stayed motionless and panting to make up for everything that had just happened.

"I guess we're even now, hm?" She asked rhetorically. "Not for long." Ash replied quickly with a newfound sense of control. He ripped off the clothing that still clung to Dawn got onto the bed with her. He shoved her down onto all fours and positioned himself behind her.

It was basically like doggy-style, only Dawn's face and forearms were flat on the bed. Her back was pretty heavily arched in order to get to the height that Ash needed it to be at. She felt Ash re-enter her from behind and immediately started to groan some more.

Ash went ahead and picked up right where he had left off. He pumped in and out at a fairly fast pace, with deep, vigorous shoves. He was going to make sure that Dawn wouldn't be able to ask for anything more this session.

Dawn was already letting out some fairly loud moans, only they were muffled by the sheets this time. Ash liked the sound of her yelping, though, and decided to increase the pace even more. Just as he had hoped and expected, he could hear Dawn raise her volume.

"OHHH! OHH! OH!" He could hear her scream out again and again. She was absolutely loving it. She was unsure how many times that an opportunity like this would present herself; she could only hope that she might have the chance to have a time like this again.

They kept on like this for multiple minutes, and soon they both found themselves on the verge of climaxing again. With both of them being as competitive as they were, they made sure to hold off as long as possible.

Since he knew that the timer was getting close to the end, Ash started to use even more energy so that he could go as fast as he possibly could. He was going to leave it all out there; this was going to finish with an exclamation mark.

"AHHHHH! OH ASH! OHH! OHH! AHH!" Dawn was screaming at her maximum volume, but luckily for Ash's ears sake the noise was cut in half because she was yelling right into the bed. Possibly because he forgot that they were in a hotel room and there were other people on the floor, Ash pulled on Dawn's straightened hair so her head would come up.

"OHHHH! OHHH! AHHH! YEAHH! YEAH! OH YEAH!" Her shrieks echoed throughout the room. She tried to keep fighting, but in the end, it was a losing battle. There was no way that she would be able to outlast Ash.

"AHHHHHHHHHHHH!" She gave off one loud, definitively last, yell as she let off her second orgasm. The expelling of her juices and the tightening of her inner walls spawned Ash to finish as well. His semen shot into her pussy, while her juices sprayed over his cock.

Ash pulled out and laid on his back. Dawn flipped onto her back too, and they both laid there, saying nothing. Both of them were thinking the same thing; is there a way that I can go back and live these past few days again?

With all of the magic that the two of them had been a part of in the past 48 hours, it was safe to say that the only word that could come close to describing their happiness would be; exuberant.

* * *

**A/N: I barely got this done in time, but hey, it's still Sunday! 11:50 p.m., but still Sunday. Well there isn't much to say but I absolutely hate this chapter. The transitions were awful and the ending was soooo forced, but at least it's done.**

**Amourshipping won with a whopping 14 votes! Ikarashipping came in second with 6, so I'll be sure to give it another chance. Let's get this many votes again guys, I was very happy with the turnout! The options for chapter "G" are:**

**A. Handymanshipping (Tracy and Daisy) B. Oldrivalshipping (Gary and Leaf) C. Negaishipping (Ash and Iris) D. Brunettshipping (Gary and May)**

**I'll be out of town and unable to work this upcoming weekend, so you guys might have to take a rain check on the next chapter; sorry! If I am unable to upload this Sunday, then I will upload twice the following week to make up for it.**

**Hope you had a Happy Valentines Day!**


	6. First

**A/N: Sorry for missing out on last week's update. I spent this week in the hospital, so I was unable to get the two updates that I had promised. I'm sorry for the false promise, but I'm happy that I even managed to get this finished with everything I had going on. Anyhow, this chapter is Amourshipping; Ash and Serena.**

**First**

Ash couldn't believe his eyes when he walked into his house for the first time in a few months. He had just returned from his attempt at the Unova League and had come home alone, as Iris and Cilan had each gone their own way. He decided that it would be best for him to come back home and think things out for a while before he rushed off into his next journey.

Much to his surprise, not only was his mom sitting in the living room waiting for him, but his childhood best friend, Serena, was as well. They both gave him a smile simultaneously as he paused in his shock. He hadn't seen her in forever, and part of his brain told him that his eyes were deceiving him; she couldn't really be there.

He soon accepted that she was there, and finally found it in himself to say hello. Once he did, Serena locked her light blue eyes into the magnificent brown eyes that had enticed her childhood. A big, goofy smile spread over both the united friend's faces, and they took off for each other at the same moment. They wrapped their arms around each other in a fit of joyous laughter.

XX

Hours flew by for the trio as they caught up with one another. There were plenty of stories to be shared and laughs to be had. Along with each other's company, they were able to enjoy a delicious homemade dinner made by Delia. She had prepared quite a banquet in honor of Ash's return home.

Once everybody had finished eating and the lively conversation slowly started to dwindle down, multiple hours had passed and the time was approaching 8 o'clock. Upon seeing the clock, Delia realized that much more time had gone by than she had thought and that she was running late.

"Oh! I almost forgot about my book club meeting! I've got to run sweeties, I'll be back in a couple hours!" Delia sang out as she grabbed her purse and rushed out of the house. The kids could hear the car door slam from inside and the engine revved up, signaling that Ash's mother had departed.

The two of them decided to keep on talking, but they moved the conversation back to the living room couch. They visited their childhood again, reliving the stories of the past. There certainly were some unforgettable memories that had been shared; times that had given them a strong bond.

"I've really missed you, Serena" Ash said with a small smile, honesty filling the low tone that he had spoken with. She held a special place in his heart that no Misty, May, Dawn or Iris was able to replace. He wasn't sure of the reason why during his first few journeys, but he felt that he was starting to understand it now.

"I've missed you too, Ash. A lot." Serena responded in a soft voice, filled with truth just like Ash's. There had been nights when she couldn't sleep due to her thoughts about him. He had crossed her mind at least once a day since the two of them were separated. She had long since come to terms with the fact that she had a crush on the aspiring Pokémon Master.

For the first time since Ash had entered the house, the room fell quiet. They had steered the conversation down onto a new path, and they were unsure of where to go with it now. Ash bit his lip in uncertainty as Serena looked down rather shyly, avoiding Ash's eyes on her. Finally, she decided that she needed to say something.

"Ash, what would you say we are?" She began with the silent intention that he not answer immediately. "I mean, we're best friends, right?" She finished with a question that she assumed was an easy yes. "Of course!" Ash responded, his eyes lighting up once more. He was very sure of that answer, but he was slightly unsure of where this was going.

"Are we more?" Serena asked simply, not wanting to spend too much time beating around the bush. Surprisingly, Ash didn't seem bewildered by the question. He exhaled, pursed his lips, and begged for his brain to send him the correct words. He thought that he knew the answer, but putting it into words was so difficult for him.

"I think… I- um… you're different. Special. I mean, I like you in a different way than all my other friends. It's sorta like how I feel towards my mom, but so different! I-uh… I think I like you. You know, like like you, not just like you, but um- yeah." He finished his rant full of stumbles with a scratch of his head.

Serena giggled at the struggles of the raven-haired boy sitting next to her. "Well I'm glad you feel that way, because I do too." She said sweetly as she scooted closer to him. She didn't want to make him too uncomfortable, but she wanted to make sure that they were on the same page with their feelings for each other.

Seeing that Ash didn't tense up any as she snuggled up next to him, she progressed to the next step. She leaned her head in and kissed him. Initially, she had planned for it to be a brief peck, but after the sensations that flowed through her body as her lips connected with his, she didn't break away. As she expected, Ash didn't immediately respond to her bold move.

Eventually, Ash did react, and his reaction was to kiss her back. The background world fell apart for the lovers as they became enraptured in solely each other. Every sense was brought into pleasure by this. The soothing sound of the fireplace and nothing else to break the peace, the smell of one another; Serena smelled like strawberries to Ash, the feeling of heat and passion racing throughout their bodies, the taste of each other's sweet lips, and the beautiful visions seen with their closed eyes.

Much to the dismay of both of them, their need for air required that they break the kiss. They locked eyes once again as they opened their eyes back up. Craving more, Serena wrapped her arms around Ash's neck and began a kiss with even more meaning. This kiss had just as much passion within it, but it had a lot more fire behind it.

Serena opened up her mouth and invited that Ash to poke his tongue inside. He jumped on the opportunity, and opened up the same chance for Serena in the process. After exploring the new territory, the competitive youngsters started to try and win the battle between their tongues. Neither had much luck in that aspect, they mostly stayed even.

The intensity rose with every second that they continued. Eventually, Serena slid her hands up to knock off Ash's hat, cueing him to do the same to hers. They then pulled their lips away, taking in big gasps of air. Afraid to ask any more questions, Serena used actions instead, and unzipped Ash's jacket. No resistance was offered, so she went ahead and got rid of his black undershirt as well.

Wanting his turn, Ash stopped her from going any further, and pulled off her skirt. He continued to peel clothes off her until she was topless, just like he was. After removing her magnolia pink bra, her breasts, roughly a B cup, were showing. He gazed at them with admiration; they weren't perfect, no, of course not, but they passed his eye test.

He softly pressed his hands up against them, he had to be gentle with these delicate objects that were foreign to him. He caressed them slowly, running his hands in small circles. Soon, he used his index finger and traced over the same pathway with them. As he brushed up against her nipples, he couldn't help but notice that they had become hard.

Serena emitted a few small groans as Ash began to throw in a couple of light squeezes. His curiousness and want for experimentation caused him to bring his mouth down upon them. He sucked, licked and continued to squeeze on them, causing for Serena exhale's to sound more and more like pleasure filled moans.

Ash used his idle hand to slowly trail down her stomach, before reaching her underwear that was becoming increasingly wet. He teased her slightly, rubbing his fingers over her covered crotch. Despite her attempts to remain calm and normal, Serena started to voice more frequent gasps through her bit lips.

"Enough! Just give it to me already!" She voiced as she became impatient. Ash smirked to himself, but stood up nonetheless and took off all his remaining clothes. As his cock came into view, Serena realized that she wasn't the only one horny, he was at full mast himself. She estimated that he was about 6 inches in length, nothing huge, but she was actually kind of thankful for that.

She slid her panties off and threw them over by her bra that matched them, but left her long, tight, black socks on. A little unsure of how exactly there were going to do this, Ash hesitated before choosing to lay out on the couch. Serena positioned herself on top of him cowgirl style. She slid down about part way, before she felt her wall block her off from going any further.

"Break it, baby." She stated with as much false composure as she could muster up. She closed her eyes in advance, but once Ash broke through, they shut even tighter as she winced from the sharp pain. She clamped her jaw down while also clenching onto a nearby pillow; there was a strange desire for her not to make any sounds. She was going to defeat this pain silently.

Once he felt Serena relax and give him a small nod of her head, Ash pushed slowly into her. After he did so, he closed his eyes because of the immense bliss that had overtaken him. Not that he'd spent any amount of time imagining it, but it was a far greater feeling than he could have imagined. He fit inside of her perfectly; a tight, snug fit.

The feelings were even better for Serena, due to the excruciating pain that preceded it. Even though that pain was terrible, it was already worth it. The closest she'd come to this feeling was when she fingered herself that one time, but that majorly paled in comparison to having a penis inside of her.

With this new sexual connection, they were both complete. It was like piecing together the last two pieces of puzzle, and the result was  
beautiful. This wasn't a one-night stand, a drunken hookup, or simply physical desires. No, this was, strictly as the word implies, love-making. It had the same electricity, fire and passion of their kissing, but took to a whole new level.

Serena started to slowly grind up and down on Ash's member. This multiplied the magnificent feelings that pulsed through her blood. She resumed the moans that she had started earlier in the night, though these were louder and represented a far more wonderful feeling. She was so in love with this feeling; she couldn't get enough of it.

Ash started to buck his hips in sync with Serena. The tempo had begun to quicken a little; Serena's grinds had started to turn more into bounces. They both found that the quicker they went, the more enjoyable it was. Soon enough, Serena was full out riding on Ash as he gave short pumps into her.

"Ohhhh. Ohhh. Ohh. Oh yeah that's good!" Serena let out as she continued to bounce up and down on Ash's dick. She was going fast enough now that her boobs were shaking some. She leaned her head back in ecstasy as she let the feeling flow through her body, filling her with a joy that nothing else could give to her.

Ash was releasing constant deep groans of his own as well. Taking the final step with the girl that he had only recently realized that he was deeply in love with was emotionally satisfying, but the physical joy that came along with it brought pleasures equal to and possibly greater than that. Since she had never been penetrated, she was incredibly tight, and that tightness caused for indescribably good feelings.

"Ahhh. Ahhh. Yess! Mhm! It's so good!" Serena continued to voice her pleasure as she began to bounce as fast as she could. Both of the lovers could feel their oncoming orgasms beginning to accumulate. Each second was better than the last, but at the same time, each second was another tick on the timer.

"Oh god, Ash! It's coming soon!" She warned the boy as she knew that this couldn't go on much longer. She tried to put this thought behind her though, the thought of the end brought a dark cloud over the gorgeous rainbow.

"Oh, Serena! I'm almost there!" Ash echoed her statements moments after she had said them herself. He wanted for them to finish at the same time. He didn't really know why, but that was the only ending that he wanted.

Seconds later, Serena lost control and let her juices fly out of her. Her climax served as the last straw for Ash as well, and he sent his seed shooting into her. They both started to breathe heavily now that they had finished what was more physical exercise than either of them had thought. After several more seconds, they were able to come back down for Earth, and Serena got off of Ash before snuggling up next to him.

"I always knew that you'd be my first. Other guys have tried, but you're the only man for me." She breathed out happily.

"You always have been, and always will be, first." Ash responded back to his new girlfriend.

* * *

**A/N: The sex scene was shorter than I had intended but oh well. Tried to make this way a little more emotional and about love then usual. Hope I did this quickly growing shipping justice.**

**Brunettshipping edged out Negaishipping by one vote so Gary and May will be the pairing for chapter "g". Options for chapter "h" are these:**

**A. Tracy and May **

**B. Dawn and Paul **

**C. Drew and Misty **

**D. Giovani and May/Dawn/Misty? If you want to specify which of these girls you want, you can. I'd be fine with any one of them, any combination of them or even all three of them. **

**Thanks for reading! Have a great day!**


	7. Girls

**A/N: School sucks. I'm so ready for it to end. Well, there's my life update for you guys. This chapter features Gary and May. I know that he didn't in the anime, but I have Gary traveling through Hoenn as Ash's rival for this story. I'm writing this in 11 point font. Take that MLA format.**

**Girls**

Gary could pick up just about any girl that he wanted to. He was blessed with his good looks, and was also equipped with a mouth full of smooth words and phrases that could woo the prettiest women. Because of this, and the fact that he was an excellent Pokémon trainer, girls flocked to him. He even had a group of cheerleaders accompanying him on his quest to become the new Hoenn champion.

He'd slept with each of them before; he even had one amazing night with all of them. He never looked for anything like a serious relationship, which bugged a lot of them, but none of that mattered to him. He was the stereotypical womanizer who didn't seem to look beyond a girl's outside appearance. There was one girl, however, that really interested him. Unfortunately for Gary, this girl was traveling with Ash instead of him. He intended to change that.

He had just defeated Ash in an intense battle on the outskirts of Mauville Town. The battle had lasted for at least an hour, and darkness had fallen by the end. Even though Gary wasn't traveling with Ash and his friends, he decided that he would go to the Pokémon center with them because it was getting late and the Pokémon center was certainly better than camping out.

As usual, Ash and Brock got a room card for the room they were sharing while May got a room of her own. Gary got a room of his own as well; his was down the hall from his frenemies. Gary got back to his room, threw his stuff on the ground, and flopped down onto his bed. He picked up the remote and hit the power button multiple times, trying to get the TV to turn on. After concluding that it was broken, he frustratingly got up and went out to the lobby to watch the TV in there.

He sat down on the couch and half-listened to the news for about thirty minutes before May came out and joined him. His eyes widened in surprise as he realized how lucky he was. He couldn't have drawn up a better situation to get the girl alone if he had tried. He quickly came up with a plan in his head, and then cleared his throat before going ahead and putting the plan in action.

"What are you doing out here?" He started up the conversation as casual as he could.

"I could ask you the same thing," She replied, not willing to answer the question simply.

"Well my TV wasn't working so I came out here. Your turn," Gary prompted her, unfazed by the fact that she wasn't seeming to be an easy hook.

"My room doesn't even have a TV. And I wanted to see the weather for tomorrow," This time May actually answered the question, clearing the first obstacle in Gary's plan.

"So what's it like traveling with Ash?" Gary asked as he sat up from his slouched position, and scooted closer to May as discretely as possible.

"Umm… It's pretty good," She answered as she started to full uncomfortable. Gary had never talked with her before this, and she wondered why he decided strike up this conversation.

"Are you and him pretty close?" Gary continued to question her while he continued to inch closer to her, though she had yet to notice that part.

"I guess so…" She said, trailing off as her comfort level still failed to improve.

"Are you guys going out or anything?" Gary asked, now officially moving the conversation down the road he had paved.

"No," She answered, she had now given up on getting the weather forecast.

"You ever been with a man?" Gary fired off another question immediately after she had answered the last.

"No!" She responded firmly, scooting over as she now noticed how close the two of them were.

"How has a girl with looks like yours never been with a man? He asked undeterred, closing the space that May had just created.

"I don't know! There's never been an interested guy I guess… not that I've been interested either," She answered yet another question, and now scooted to the edge of the couch to create space once more.

"Well I'm certainly interested, and I think I could interest you too," Gary said, revealing his motives behind the "friendly conversation".

"N-no! I'm sorry… but I just… no," She said in hopes that he would stop talking and leave her alone.

"Come on baby. You ought to give me a shot," He said as he put on hand on her side. He leaned in to the point where he had invaded May's personal space and she could feel the warmth of his breath on her face.

May looked around in hopes that somebody was in the room or would enter the room and stop this from going any further. Unluckily for her, it was only the two of them. Gary was now rubbing his hand along her sides, and as much as she hated herself for it, she silently enjoyed it. With his experience, Gary was able to read her face and know that he was succeeding. He went in for the kill; he leaned in and kissed her on the lips.

"Why don't we take this back to your room?" He asked, thinking that he might just have it in the bag at this point.

"N-no… I couldn't do that..." May rejected his request, but it was an extremely weak request and was not enough to get him to stop. He now kissed her cheek multiple times, getting no resistance from May.

"Fine. Then let's take it back to my room, sweetie," He smoothly responded as he trailed his kisses down to her neck.

May said nothing this time, she could deny him no longer. Her teenage hormones were raging now as Gary gave her her first hickey. It felt so warm, so new, and so good. She let out a soft moan, which basically served as a white flag in Gary's eyes. She had finally given in; he had done it once again. His ego managed to soar even higher upon this realization.

Once Gary had finished his job, a job that would probably be difficult to explain in the morning, he guided May off the couch so he could lead her back to his room. He snuck his hand down onto her butt, feeling her up along the way, as May continued to let Gary control her. She didn't know why she was letting all this go on, for some reason she blindly trusted him to make her feel good.

He unlocked the door, and closed it right back after they had both entered. He pressed his lips back on top of hers, and let his hands do some moving. He brought one back to her tight butt, and used the other to begin removing clothing from the girl under his spell. He removed her signature bandana, and all of the buttons on her shirt before snaking his hand up her shirt and feeling the two things that truly separated May from most girls her age.

There was plenty of heat in the room now, with most of it being emitted from the kissing being done. May knew that it lacked the true electricity of a loving kiss, but the heat alone felt fantastic. She barely even noticed that her clothes were slowly but surely being removed for her. Eventually, Gary withdrew from the kiss that he had initiated.

He ripped off the shirt that he had unbuttoned, and her bra fell down too as he had managed to unclip it while he was fooling around in there. In order to make her feel a little less bashful, Gary removed his own shirt after this. She didn't have any reason to be self-conscious he thought, she had a rack that was surely the envy of all the girls her age.

"Oh good god…" he muttered out as his suspicions from seeing her with a shirt turned out to be false. She didn't stuff her bra as he thought she had; she was perfectly natural. She hadn't even been wearing a push-up bra; she was simple blessed with large, firm tits. He could have fun with those babies all day, but he'd already gotten what was his fair share of fun with them for the night.

Instead, Gary continued undressing himself, taking off his dark blue jeans. His black briefs that he had underneath didn't stay in sight of very long, as they were discarded quickly. This action revealed what Gary had self-described, and many girls had seconded, as a beast. His current length would already qualify as big, and he wasn't even fully erect yet.

Gary put on his often present smirk as May gaped. She had told the truth when she said that she had never been with a man, but she'd watched a few videos that were supposed to have been for adults only, and she'd gotten her hands on toys that actually weren't meant for kids. She knew that she was going to have trouble fitting him inside of her.

"I think you know what to do with it," Gary commented as May had started to get over the shock of seeing her first human penis. She did, indeed, know what to do with it thanks to those naughty videos. She opened her mouth and slid it over the front half of his rod. She wasn't sure what she expected to have tasted, but she was happy to find it to be a nice taste.

She closed her eyes and tried to tell her mouth that she was simply sucking on a lollipop or a popsicle or something like that. She sucked on it, and gave her tongue the most exercise that it had seen by moving it along everywhere that she could reach. Each second proved to provide valuable experience as she improved at a modest rate.

Gary, with all of the different girls that he had slept with, had received many better blowjobs, but for a first-timer, May was performing at a slightly above average level. She began to take in a little bit more of him when she felt that she could do so without choking on it. She dare not even imagine of going all the way down on him. She just worked with what she could at this point in time.

Even though she hadn't done a job that he would remember down the road, she still accomplished the goal that he had silently set for her. His cock was now popping out its full length, extending a foot from the rest of his body. He eyed May's shorts, and she got the message right off. She slid her biker shorts off, and her red panties followed them to the pile of clothes that had accumulated.

May lied down across the bed, and Gary crawled in behind her. Without bothering to ask, he slowly inserted himself, waiting for her hymen to stop him at any time. Much to his surprise, it never happened, as unbeknownst to him, it was already broken. Being presumptuous, Gary immediately assumed that she had been lying earlier.

"I thought you said you hadn't been with a guy," He said in a questioningly manner.

"I hadn't! Not until now anyways… but I've done some other things," She said as she let Ash's rival in on her dirty little secret.

"Well aren't you a naughty little girl," Gary said as another smirk came onto his face.

He then began to slowly pump partially in and out of the amateur. He wasn't going to go all in on the poor girl; no he wasn't that much of a jerk. Ok, maybe he was, but he wanted to be as nice as he could to May. He didn't want this to be a one night stand or anything; he wanted to sleep with this beauty as many times as he could. He didn't want an actual relationship of course, but she had all the assets that he could want in a sexual partner.

May let out some long, soft moans as she lost her virginity while Gary was also unable stay silent due to the pleasure of entering into a girl so tight. He'd had the pleasure of popping the cherry for many different women, and the experience never got old. He didn't understand why any guy would want to be with an overused, loose girl, because this felt amazing.

Once he thought that he had given her sufficient time, Gary began to penetrate in just a little bit deeper, now over half of his length, as he wanted to explore the depths of her vaginal canals. It seemed that the further in he went, the tighter and more fantastic it felt for him. He hoped that May was getting the same utter enjoyment out of this as he was, and by the sounds of her moaning, he assumed that she was.

"Oh it feels so good!" She let out softly in the midst of her pleasure. When she first discovered the "art" of masturbation, she thought that it felt really good, but actual sex was on a totally different level. Gary's meat barely even fit inside of her, and caused for her insides to be stretched to levels that they had yet to stretch to.

Every couple of minutes, Gary would add in another inch or so, multiplying the joy for each of them every time that he did so. Though he tried to keep them in, Gary had to give off grunts as his cock was squeezed as tightly as it had ever been. He had also been increasing the very slow pace, but he still kept it fairly slow.

"Oh you're so big! Oh! Ahh! I think I'm going to cum!" She announced as she tried to hold in her climax for as long as she could. Gary didn't really heed any mind to what she had said, he only thought of what she would say if he actually put all of himself inside her. He stayed patient though, for he wanted there to be a sequel to this sometime in the future.

"AHHHH!" May let out her first real scream of the night as she orgasmed. It was much more powerful than any of the finishes that she had gotten when she was by herself. After getting over the thrill of how wonderful it felt, she realized that Gary had managed to hold it in, and that meant that they weren't done just yet.

May returned back to her knees in hopes that she could give Gary the same finish that she had gotten. She picked up right where she left off, remembering the lessons that she had taught herself earlier that same night. She still could only fit in about three-quarters of him, but she hoped that maybe by next time she would a find a way to fit all of him inside her mouth.

Gary, on the other hand, was no longer satisfied with what he was getting. He decided that it was time for him to take control. He grabbed the back of May's head and forced her to go all the way down to the very base of his cock. He could hear her gagging because of the unexpected move. She thought for sure that she was going to choke if he kept her like this.

Much to her relief, Gary released and allowed her to come back up and get some air. He only gave her a couple of seconds, however, before forcing her back down. She wasn't ready for this one either, and started choking again, although she probably would have choked regardless of if she was ready or not.

Gary repeated the procedure, and started to quicken it as well. Surprisingly, despite all of his times with women, he had never skull-fucked any of them. He didn't even know what had given him the idea to do it, but he was glad that he came up with it. May continued to gag as his huge dick continued to force its way down her unready throat.

May didn't understand how girls learned to breathe like this. Her whole mouth was stuffed full and Gary's cock went down and seemed to block her air passageways in her throat because of its extensive length. He would pull out momentarily, just long enough for her to take a tiny breath, before pushing his way back down.

"You like that, don't you, you little slut?" Gary said in a jesting manner. May wasn't sure how long she would be able to stay conscious if her breathing continued to be cut short like it was now, but she just hoped to tough it out until Gary finished with her. She wouldn't have to wait too much longer, Gary knew he couldn't hold it in for very long.

Knowing that he had only seconds left, he got a little rougher with her. He pumped in a few more times, pushing in as far as he could. Finally, when May was probably a good minute or two from fainting, Gary reached his climax. He released his seed with his cock still lodged in her throat. She was forced to swallow it; it didn't taste that bad though, so she didn't care.

Gary then took his hands off of May's head and pulled out of her mouth. She coughed multiple times, and took as many deep breaths as she could. They stayed silent while May tried to return her breathing back to normal. Once she finally had, she began to redress herself. Before leaving, she felt the need to ask Gary something.

"So am I just another hot girl for you to sleep with for one fun night?" She asked in a way that it was more of a statement.

"Of course not," He responded coolly, in hopes that she wouldn't hate him. She arched her eyebrows, before escorting herself to the door. When she reached to turn the doorknob, Gary called out to her for one final time.

"Oh, by the way, it's supposed to rain tomorrow,"

* * *

**A/N: See that mini breakage of the fourth wall? More like a little dent? The line about wanting a sequel? Yeah I'm planning to write one at some point. In good news, I got this written by Saturday night, so I didn't have to rush to beat the deadline! Tracy and May picked up 9 votes and won the fan poll. Here are the options for chapter I:**

**A. Ash and Cynthia B. Giovanni and Delia C. Jessie and James and Jenny (Or just James if you prefer) D. Trip and Iris**

**Make sure to vote, and all reviews are very much appreciated! Hope you enjoyed this chapter!**

**Have yourself a wonderful day**


	8. Handyman

**A/N: I realize that handymanshipping is Tracey and Daisy, but I still called this chapter handyman even though it is Tracey and May. Because he's still a handyman. And I'm uncreative like that. Oh yeah and I don't remember exactly how the start of Season 9 started, but I hope that I'm relatively close to accurate.**

**Handyman**

Ash and his friends had just wrapped up their adventure in Hoenn and decided to travel back home to Ash's home in Kanto. After visiting with his mom and taking a little bit of a vacation, Ash heard about the Battle Frontier and knew that it was for him. He decided that that would be his next challenge, and his friends decided to keep traveling with him for the time being.

Before they departed to find the first Frontier Brain, Ash wanted to stop in at Professor Oak's lab so he could see some of his old Pokémon. When they knocked on the door, Professor Oak didn't answer, but Ash's old traveling partner, Tracey, did. Tracey was now working alongside Professor Oak as his assistant. Ash introduced his new friends, May and Max, and they started talking about everything that had gone on since Tracey had stayed behind at the lab.

After he remembered why he had come there in the first place, Ash went out into the field so he could find Professor Oak and all his old Pokémon. Max, very excited at the thought of seeing more new Pokémon, went out with him. Brock, who was closer with Oak than he was Tracey, went out with the other boys.

Tracey and May continued the conversation on their, finding out that they had quite a bit in common. Needless to say, a connection was made, and they really hit it off. Tracey ended up offering a tour of the lab to his new friend, who eagerly accepted. He showed her some of the not top-secret research that had been going on, and introduced her to some Pokémon that she had yet to see.

The last room that they entered was a room that was fairly empty. It had a big window overlooking the gorgeous fields full of the lab's Pokémon, and other than that, it simply had a stool and a bunch of paintings. The paintings were all of different Pokémon, and May thought that whoever made them must have been extremely talented.

"Did Professor Oak buy these?" She asked in her curiosity.

"No, I made all these. I know they aren't great or anything, but art is my passion," Tracey answered honestly.

"Are you kidding me? These are fantastic! You have a ton of talent," She gushed heavy praise out.

"Gee, thanks!" Tracey muttered out, slightly nervous as his face turned to a light scarlet red shade. May started to go up to each individual painting, wanting a zoomed in look at all of them. Tracey walked up behind her as she spent an extended period time in front of one particular painting. He brushed his arm up against her shoulder as he pointed to the different Pokémon in the picture, giving her the names to the ones what she probably hadn't come into contact with yet.

May turned around to respond to him, but shut her mouth once she realized just how close that they were. Tracey hadn't intended to get in her personal space, but he now realized the very close proximity of their faces. Neither of them moved for multiple seconds; reading the other's face and staring into each other's eyes. Something clicked for them simultaneously, and they closed the short distance between them.

The two of them were exposed to some foreign feeling as their lips connected. Tracey, who didn't consider himself a smooth guy, was shocked at his own boldness. He asked himself in his head if he had actually just done what he had done, and if this was real, before coming to the conclusion that he didn't care. May didn't question the reality of the situation, but she was in disbelief as well. However, she took the some mentality the Tracey had; just enjoy it.

Messages seemed to be communicated through the electricity that was sparked by their kissing. The messages being sent were those of hunger, so Tracey pushed the action forward. He brought his right hand down and brought it back up underneath May's red shirt. He started to pull up on it, and soon got some assistance from May. They parted their lips very briefly as they slipped her shirt over her head and flung it carelessly.

Seconds later, May copied Tracey's actions, and they parted once more so that they could remove his shirt as well. May started to poke around at Tracey's belt, doing her best to get it off. Tracey dedicated himself to a simpler task, and reached back to unclip May's lime green bra off. He discarded it and began to fondle her. As he continued to play with her, he wondered to himself if she was still developing, because it was hard to believe that she would develop too much more.

After a minute or two of struggling, May managed to complete her job, and consequently, she dropped Tracey's baggy shorts onto the ground. She could feel his throbbing member was being confined inside his constricting underwear, so she tugged once more, causing for Tracey to become completely nude, minus his shoes. She then started rubbing her hand over his crotch; taking her own turn to play around.

Eventually, they separated from each other's lips for good. Tracey gave a disapproving look as he saw that clothes remained on May; that wasn't going to work. May knew exactly what he wanted, and she began to remove her shorts. She turned around and bent over in the process; purposely giving Tracey a wonderful view of her cute butt. She jiggled around just a little bit, trying to arouse Tracey even further. It worked perfectly; his eyes bugged out when he was that her back was just as nice as her front.

She gave an almost arrogant smile; she wasn't actually arrogant, but she wasn't modest when it came to appearance. She knew she was hot. She wiggled her way out of her skimpy green panties, taking more time than what was actually necessary. After she took her sweet time bring them down to her ankles, she kicked them off, causing them to fly across the room to join the rest of her clothes.

"What do you want do to me?" She asked in a seductive tone, pressing against her own breasts, "What do you want to do with this?" She questioned again as she rubbed her hand up and down the length of his hardened cock. She got down onto her knees and licked her tongue across his shaft. She ran it over his length a couple of times, but before she covered it with her mouth, Tracy decided that he wanted something else.

He leaned May back, spread his legs, and pressed his dick in-between May's melons. He slowly rubbed it up and down on her chest. She picked up on what was going on quickly, and pressed her tits against his cock. Since her boobs were safely on the large side, she had enough to completely smother him in her breasts. Tracey was grunting heavily he kept pushing his erection up against her fantastic titties.

As previously stated, Tracey wasn't too great with girls, so he was in still in awe of the situation. It was like he had gotten the hottest, most sought-after girl in school, and was getting to do whatever he pleased with her. He wasn't sure what was so attractive about boobs, I mean weren't they just balls of fat? But either way, looking down at his cock snuggled up inside of those treasures nearly made him bust a nut.

He was, in fact, getting close to doing just so, so he reluctantly retracted from his paradise, and inserted himself into May's mouth. She didn't waste any time, she immediately began bobbing her head up and down while using her tongue to pleasure Tracey all around. Tracey wasn't exactly big, but he wasn't small either. Since he was only average in his length, May was able to engulf all of him.

She would barely even gag when the tip of his cock would find itself at the back of her throat. She could take him in comfortably, which allowed for her to focus entirely on the work of her tongue. This was plenty enough to finish the inevitable that Tracey was postponing for as long as he could. He'd never had a blowjob, much less been deep throated, and found himself unable to keep his cum in any longer.

He shot his hot load down her throat, and she swallowed it without as much as a blink of the eye. She smiled inwardly, proud of the work that she had just done. Tracey pulled himself out of her mouth, and much to the relief of both of them, he was still erect and ready for more. Tracey silently thanked god, he would have been extremely embarrassed if they had to stop after that.

"Mhm that was tasty. But my little pussy is hungry for your cum too," May growled out, ready for her wet pussy to finally get its fill.

"This might hurt…" Tracey said weakly.

"Oh you're not my first. A girl like me doesn't stay a virgin very long you know," She said, again not afraid to reference the fact that she was a wonderful piece of eye candy. She didn't mean to come off as a slut; she really wasn't one, but she'd been penetrated twice before.

Tracey nodded silently; it didn't bother him that she had already slept with someone else, it was just a little bit surprising. She was right though, she could probably seduce any straight man that she wanted to. He proceeded to push her into bending over his stool, the lone piece of furniture in the room, and positioning himself behind her.

For the who-knows-how-manyth-time of the day, Tracey's eyes bulged out in a happy surprise. Even if this wasn't her first time, May was still plenty tight, and it felt like heaven down there. He pushed in further, all the way in, and marveled at how the wonderful feelings grew exponentially. He pulled most of the way out and reinserted himself, still attaining the same level of amazement the second time around.

He repeated his motions a couple more times, before he started to complete the process a little bit faster. Just like anything one does for the first time, Tracey was able to do it faster the more comfortable he became with the foreign process. Before long, he had established a bit of a rhythm at a modest pace. At the time, he was moaning even louder than May was.

Tracey didn't like that this was the case, and so he started to go just a little bit faster and he began thrusting just a little bit harder. As he expected, May raised her volume a little bit in correlation with his adjustments. This made him happier; therefore, he did the same thing again. He started to go balls-deep with rough thrusts.

"Oh yeah! That's it! FUCK! OH! Fuck me harder! Oh god, faster! YES!" May was now bellowing out screams that would have been heard if there was anyone else in the lab.

Tracey was happy to comply with the brunette's wishes. Before he did, however, a thought came to him. Smiling mischievously, he retracted from May, earning a disapproving huff, but put himself back in quickly. This time however, he was entering inside her butt. He could barely get his cock inside of her dainty, tight ass, but he made it fit.

"OH SHIT! Oh it's so big! I've never done anal… oh make me scream," She pleaded, knowing very well that she would get what she was asking for.

Tracey's cock was getting clamped on even tighter than before, it was like a Pokémon was using vice grip on him or something. He picked up where he had left off though, giving her rough thrusts that were sure to get her squealing. He pushed in as deep as he could, surprised at how far he was able to get to. Pumping away, Tracey finally felt a small sense of control over the situation for the first time since they began.

"YES! Oh yes! Oh god!" May resumed the screams that had gone on a brief hiatus. She loved the novelty of what they were doing; she was always up for something new. Especially if that something happened to be as pleasing as this was. Her breasts would have bouncing had they not been pressing into the wooden stool that she was bending over.

"OH FUCK!" May didn't announce that she had climaxed, and Tracey had no way of knowing so, but he thought that she might have. He hoped that it was that way, because he was about to finish, and he didn't want to leave her hanging. He brought his thrusts up to an even faster speed, and a roughness that he had yet to attain.

May's yells seemed to be in the background because of the fact that Tracey was focused strongly on what he was doing. He gave her a loud slap on the ass at the same time that he entered in as far as he could for the final time. He released his seed deep inside of her anus, letting out a final grunt of his own. He was disappointed that he had finished earlier than he had hoped, but he was still happy because of how great the experience was.

May stood up and was about to say something, when they both heard voices becoming louder, and the opening and closing of the back door. They put on their clothes in a panic, they had forgotten about the boys that were out in the field. Thankfully, they managed to get dressed before the rest of the group managed to track them down.

A mere 15 seconds after they finished removing any evidence, the four guys poked their heads in the room, ending their search of the two that had stayed behind.

"You guys missed out on a great time!" Max started, before rambling on about all they had done to five pairs of inattentive ears.

"Oh we had a great time in here too. Trust me," May responded, who was simply glad that her great time went unnoticed by her traveling buddies.

* * *

**A/N: I reverted back to finished relatively late on Sunday night again. Darn. Hope you guys liked it; it was fairly rushed. In other news, a hotly contested race ended with a last minute win for Jessie+James+Jenny. A few final votes today got it up to 13, with Ash+Cynthia falling just short at 12 votes. I was thrilled with all the votes that were submitted; keep it up guys!**

**Options for chapter J include the following:**

**A) Ash+Cynthia (giving it another shot!) B) Drew+Dawn C) Brock+Delia D)Butch+Cassidy**

**Oh, I was asked about Pokemon+human stories, and would like to say I haven't ruled it out yet. Not sure how well received it would be by everyone, but if it proves to be that a lot of you want to see it, then I'll start to write a few. PM with your thoughts please! Or simply add it to your review1**

**Happy Selection Sunday, a.k.a the start of greatest week of the whole year! Hope your team got in :)**


	9. Incarceration

**A/N: Please please please, if you are underage, do NOT read this. Shit gets real XD But seriously, this isn't for kids. For those who don't know; to incarcerate is to imprison. This story features Jessie, James and Officer Jenny.**

**Incarceration**

"Oh I can't believe that BITCH!" Jessie exclaimed in her rage, "How dare she arrest us? We'll show her why you don't mess with Team Rocket! Oh yes we will get revenge!" She continued with her rant inside of a prison cell that she was sharing with James, her partner in crime. Meowth had managed to escape the scene without the cops finding him, but his partners weren't so lucky.

James did not rant as much as his bossy companion, but he shared her indignation. He could not stand being locked up in a cell, especially since he had done nothing wrong. They were simply doing yard work for a poor old man who could not do it himself. Granted, they weren't doing it just to help the old man, but he was happy to pay them for the work and they needed the money.

Then, out of nowhere, Officer Jenny came charging down the street and arrested both Jessie and James. When they demanded to know what charges were being pressed against them, she told them that wearing the Team Rocket uniform warranted an arrest. Minutes later, they were thrown inside a small, three bunk bed jail cell, and they were told that their sentence was for five years!

"Five years in here, my ass!" Jessie continued to fulminate over the whole ordeal, "I won't spend another night in this damn cell!" Her temper had not gone down in the days that she had been locked up. In fact, James wondered if she would ever calm down. He began to fret over five years of putting up with that, but reassured himself that they wouldn't actually be stuck in there for that long.

"At least they forgot to search us," James said, hoping to bring a little bit of optimism into the room. Jessie turned to explode on him, but her face softened before any words came out, and instead of yelling, she nodded in agreement. At this point, it was best for them to stay on the bright side. Getting angry wasn't likely to get them anywhere.

They emptied out all of their different pockets, seeing what possessions that they had. After they were done, it didn't seem like they had much to help them escape; they didn't have any weapons or sharp objects on them. All that they had was a cloth, a pack of gum, some rope, a few Band-Aids, an empty wallet, tape, a tissue and some candy wrappers.

"What good will any of this do?" James pouted, ironically sucking a lot of the optimism from the atmosphere.

Moments later, an evil smile popped out on Jessie's face, and she said "I've got an idea. I know what we need to do," with her smile not leaving her face for one second.

XX

Officer Jenny strode down the hallways of empty cells, the only occupied one being the one that she had filled herself earlier in the week. She was carrying two bowls of soup to feed those very prisoners. She looked in the cell, and was shocked when she saw nobody in there. She gasped as she thought that they had managed to escape somehow. Little did she knew, James and Jessie were curled up tight in the front left corner of the room that was out of the field of the vision from the outside of the cell.

Officer Jenny unlocked the door and stepped inside, expecting to find a small passageway dug out through the wall. As soon as she stepped foot inside the cell, however, she was tackled onto the ground. She tried to let out a scream but her mouth was covered. Her brain then processed exactly what they had done, and the horror seeped into her mind.

She was unable to put up a worthy fight against her two opponents, and her mouth was soon covered with a white cloth that wrapped around her head with the help of a short string of rope. She soon found her hands cuffed together with a spare pair of handcuffs that she had been carrying on her belt. The two prisoners now looked down on her with matching smiles that did not give off any promising signs for her.

"Silly girl," Jessie started, "Why did you decide to mess with the almighty Team Rocket? We weren't even doing anything illegal! Well, it doesn't matter why you did it, because I'm afraid that you're going to have to pay for what you've done." She sneered out in a threatening manner. Jenny tried to come up with a rebuke, but she couldn't talk.

Jenny's eyes shot open in a terrifying surprise as Jessie and James began to rip away her clothes. Her muffled screams became dramatically louder, they would have driven a person deaf if the sound waves weren't blocked. Nonetheless, they were muffled, so her shrieks proved to be no threat towards getting the attention of a security guard or a civilian. Unfortunately for Jenny, the duo had shrewdly timed their attack while the guards were on their two hour break.

Once they finished stripping Jenny completely naked, Jessie gave a few unimpressed clicks of her tongue. "Well, it looks like you're overdue for a haircut," she commented, referring to her unshaven pussy. "We'll take care of that for you," She finished in false sweetness.

Jessie collected some of the Band-Aids that they had scrounged up out of her pockets earlier. She placed one directly over her a line of her pubic hairs, and ripped it off harshly once she had stuck it on. Muffles could once again be heard from Jenny as she struggled in pain. Jessie did the same thing twice more, until she had effectively removed the patch of hair surrounding Jenny's vagina.

"What should we do with you now?" Jessie asked herself out loud.

"I think I've got an idea," James answered for her.

They picked up the whimpering lady, and put her on top of the top bunk. James picked up the tape that lay with their assortment of "junk." He put her left foot on the far side corner of the bed, and rolled multiple layers of tape around her ankle and the corner. He took her right foot and did the same thing at the other side of the bed. Once he was done, her head laid dangling down about three feet above the ground and her legs were spread as wide as they could go.

Jessie stayed on the top bunk where Jenny was hanging from, and James got back on his two feet. He dropped his pants to the ground, and pulled his shirt over his head. He freed himself of his boxers, and the untied the rope and took the cloth out of Jenny's mouth

"You'll never get away with th-" Jenny tried to give a threatening warning, but her mouth was once again prevented from talking; this time because of James' cock being inside of it. She was utterly helpless; there was nothing she could do but take it. At the same time that James forced her to suck on his cock, Jessie got to work with Jenny's exposed pussy.

She ferociously began to lick away at her clit, which drew more muffle noises to be emitted from Jenny. She couldn't make much noise at all now, because James' cock had hardened and lengthened since it had entered inside her mouth, and now reached back towards her throat. She knew that she would get smacked, and probably beaten even worse, if she attempted something foolhardy like biting down on his dick in protest, so she did no such thing.

"Oh yeah you suck that cock, you slutty little bitch, suck it good!" James commanded in ecstasy as he reached forward roughly groped her full chest. He didn't bother being careful one bit, he squeezed, pressed, and pinched them as hard as he pleased. He'd never gotten to be rough the few times that Jessie and him had engaged in sex since she was pretty masculine herself, so he was enjoying his opportunity to do so now.

He pushed his long rod further in Jenny's mouth while putting his hands on the back of her head to give complete control. He loved the pitiful gagging sounds that she made as she struggled to take in air with a big obstacle blocking the usual path. If that weren't bad enough for her, Jessie was still lapping away at her other end.

As much as she despised herself for it, Jenny could feel herself getting wet down below. She was by no means enjoying this, but because of the stupid biology of her body, she was now releasing hormones. However, there was nothing she could do to stop it from happening. There wasn't anything that she could do, period.

"Oh you like all this don't you?" Jessie teased her as she started to realize the same thing that Jenny had. "Well, how do you like this?" She asked before inserting her index finger.

Jessie started fingering her roughly, much to the discontent of poor Jenny. She did not waste any time before adding her middle finger to join her index finger. Not long after that, she brought her ring finger in on the action as well. She pumped them in and out vigorously, causing for even more muffed up groans to escape Jenny's throat.

Much to her dismay, Jenny reached an orgasm as the intense fingering continued. She thought that there was a slim ray of hope that it would all end now that she had reached her climax, but it didn't pan out that way. Instead, she continued to lose the precious little amount of air that she had because of James' dick, and she received even more teasing from Jessie.

"Oh you just love this don't you, slut?" Jessie asked, "You want to cum for me again?" She kept teasing her.

Jenny did not even bother to attempt to shake off the outlandish claims. For one, it was not like it would help her cause, the questions were meant to be rhetorical. And two, it would not be wise for her to talk if she wanted to remain conscious. She knew that if James did not quit soon, that she would pass out. She didn't think that it was very likely that he would choose to stop.

She was correct in that matter, James had no intention of stopping. He persistently shoved his whole member forward and brought her head forward as well, getting the deepest penetration possible, thanks to the angle that she was at. If Jenny was glad about one thing, it was that she didn't throw up despite her uvula being knocked around some. It wasn't much consolation to the fact that she was choking on dick.

Even though she knew it was useless, Jenny exerted some of her energy into trying to close her legs. It was a futile attempt; the tape had her locked into position well. The ceaseless finger blasting was getting close to making her lose control one more. It simply turned into a race of what would happen first; passing out, or cumming once more. Ultimately, she ended up climaxing once more, and only seconds afterwards, she blacked out due to her lack of oxygen.

She woke about 90 seconds later, still tied up, and the cloth was reinserted. She had been moved around though; she was now hanging right side up. Her arms were taped along the railing of the top bunk, her hands tied to the opposite corners. Her brain wasn't able to process much, she was still groggy, but she had a pretty good idea of what was going to happen next. James was on his knees in the middle bed, and he lined up perfectly with her torso. Jessie remained on the top bunk, but now she, too, was nude.

Once he realized that she was up, James got right back to work. He pushed his full length in, pulled it out briefly, and shoved it right back in. Jenny let out a scream, she was finally able to get one out that wasn't covered up, and then her mouth was soon covered by Jessie's pussy. Jessie pushed on the back of Jenny's head and demanded that she eat her out.

The terror and fear had sunk so deeply into Jenny at this point that she obeyed the command without any second thoughts of rebelling. She did not have any experience in this department, but tried to mimic the tactics that Jessie had used on her earlier. After her first few swirls of her tongue, Jenny immediately was overcome by the acrid taste. It was horrible!

"Oh you love eating out my pussy don't you, bitch?" Jessie kept on with her unabating and humiliating taunts. "You've done this before haven't you? I'm sure you have. It's your favorite food isn't it?"

Jessie's accusations were so incredibly accurate, but Jenny knew she had to put up with it. She kept telling herself to not show any weaknesses, just power through; it has to end eventually. The thrashing that she was taking was hardly bearable, however. James gave no regard to the fact that her seldom used vagina had a tough time fitting him inside her, or that he was causing some intense pain. He had mostly started this ordeal just to comply with Jessie, but some strange feelings had overcome him and caused him to enjoy his dominate position.

The angle created from Jenny hanging down allowed for James to reach into depths that no man had reached for Jenny before. He had no hesitation in getting the most out of this advantage, he roughly slammed his entire member inside her, repeatedly. The pain was too much for Jenny to ignore, she had to tear her mouth away from her disgusting chore, and grit her teeth to prevent shrieks.

"How dare you stop?! I didn't give you permission to do that! You're going to have to pay for that!" Jessie exclaimed.

Jessie climbed over the railing and hopped onto the second bed with James. She said something quiet enough that Jenny could not hear, and James pulled out of her. Jenny was extremely confused as to why he did so, but felt some short relief. The relief was ephemeral for sure, James entered back inside of her moments later, but this time, it was in her other hole.

"AHHH!" Jessie let out a deafening scream as her anal virginity was roughly stripped from her. She thought that her vagina had a tough time accommodating James' size, but this was on an entirely different level. She felt her inner walls swell and stretch out further than they should, or she even thought they could. She could not even attempt to hold back from screeching painfully loud.

Because of this, Jessie hurriedly grabbed the cloth back up and put it back inside her mouth. It greatly reduced the loudness of Jenny's yells, but the muffled noises coming out were significantly louder than the ones she had made earlier. Just when Jenny thought that it was as bad as it got, she felt Jessie reenter her fingers back inside of her vagina.

She was expecting more fingering, but got a terrible surprise when she felt Jessie working around to fit her whole hand in. After some wiggling around, Jessie was able to get her balled up fist inside of her, and she began to fist her. Now that both of her holes were being filled with more volume than she thought was possible, Jenny felt a few tears start to stream down from her face.

She no longer worried about not showing weakness or pain; it hurt too badly. She openly sobbed, and her muffled screams of agony were loud enough that if anyone else was in the building, they would have easily been audible. Her pain was not enough to touch the hearts of her assailants; there was no letdown in their activity.

As her pussy continued to be violated by the rough thrusting of Jessie's hand, Jenny felt herself orgasm once more. It was the most powerful orgasm that she had ever had, but it certainly did not feel good. Jessie retracted shortly after she felt her hand get sprayed with the juices that flew out of Jenny. She got up and got back on the top bunk once more. She loosened up the cloth just a little so that she could fit her hand inside of her mouth.

"Suck your own juices, bitch," Jessie snarled out venomously.

Jessie slipped her index finger inside of her mouth, making Jenny give it a sufficient cleaning. Once she felt that she had done enough, Jessie put her middle finger in for a cleaning as well. She did the same thing until her whole hand had been licked off. Meanwhile, Jenny felt so dirty and disgusting. Sucking on her own cum? Just the thought made her want to throw up.

Before Jessie could come up with any new, cruel way to humiliate her, Jenny felt James finally shoot off his load inside of her. He had managed to abstain for quite some time, but in finally doing so, he was able to get one final climax from Jenny as well. She closed her eyes and whimpered at the extreme suffering she had just been put through. She knew by the amount of cum that had been released into her anus hat James had to be spent, and that they were done with her. Or at least close to done.

To confirm her suspicions, she felt the tape being undone from her arms, and she fell the four feet that her feet were hanging from. She was hanging right side up, but she did not have the focus or energy to land on her feet. She collapsed onto the ground in a pitiful heap. Jessie and James began to redress themselves while Jenny felt James' cum slowly start to leak out of her butthole.

Jessie piled up all of Jenny's clothes, and grabbed the key to the jail cell as well. She walked over to Jenny one more time, and lifted up her face. The face that she saw was covered in the tears that she had produced over the last 10 minutes. Her caramel brown eyes could hardly be seen through the squint and all the tears.

"You don't mess with Team Rocket, ok bitch?" Jessie cleared her point one final time before she escaped.

Jenny gave a slight, trembling nod. Jessie gave a short, satisfied snort before opening Jenny's lips with her own, and spitting a large ball of saliva down her throat. She then put the cloth back over her mouth, and tied her down naked on the bottom bunk. With that, Jessie and James left the cell for good, feeling that they had gotten their revenge.

They closed and locked the door behind them, taking the key with them. They fled the city right after they got out; they weren't sure how many minutes, hours, maybe days, it would take before someone would find out about Jenny. All that they knew was that anyone who dared try to incarcerate them was in for some big trouble.

* * *

**A/N: Let me know if that crossed the line. Wasn't sure how intense to make this when I planned it out, but that's about as bad as it gets. Anyway, it is 1 am on Sunday morning, I went ahead and wrote this instead of sleeping because I will have no time tomorrow. I've had so much crap going on lately that if it doesn't calm down, this story will go on hiatus until the summer. Not likely, but possible.**

**Rayshipping completely dominated the fanvote this time. I didn't even bother to count up how many it was. Something like 17. So chapter J will be Ash and Cynthia. This will be interesting.**

**The options for chapter K are the following:**

**A. Clemont and Serena B. Brock and Dawn C. Delia and Oak D. Ash and the Sensational Sisters**

**Any good ideas for a K word? None coming to me yet. Special promotion: Anyone who can guess which word in here was one of my vocab words gets their vote to count twice. Not sure why I'm doing that, just sounds fun.**

**Hope your bracket isn't too busted :)**


	10. Judicious

**A/N: I decided to experiment around a little bit more this chapter. This one will be AU (alternate universe), which basically means this story takes place on Earth as we know it, not in the Pokémon world. So Ash isn't on a journey or anything. I'll see what you guys think; I will do more if it is liked. The couple is Ash and Cynthia. J was a tough letter to try and find a word for. Judicious means "done with good judgment"**

**Judicious**

It was Friday, June 1st, the last day of school. Ash had completed his final exam of the year, geometry, that morning. He stuck around until the end of the day because his class was throwing an end of the year party, and he thought it might be fun. It turned out to be a pretty good time, but as the clock inched forward, everybody there was anxiously waiting for the final bell to ring.

"Can I get a kind student to stay after and help me clean all this mess up?" Ms. Gray asked, before adding "It will only take a few minutes!"

Ash was quick to volunteer, he didn't have anywhere to be so he did not mind. The bell rang shortly after, and the school's halls were soon filled with delightful whoops and excited cheers from the students who were officially on summer break. Ash smiled at the happiness that radiated from the departing student body, but then remembered that he had some work to do.

He took the trash can around the room, and filled it full of candy wrappers and other trash that the class had carelessly left sitting on the floor and desks. As his teacher had promised, it did not take him long at all to finish his part of the cleaning. She had been sweeping the floors, and upon finishing her job, she called Ash over to her desk before he could leave.

"Can I speak with you for a minute, please?" She kindly asked, though there was only one correct answer.

"Uh, sure. Is something wrong?" Ash was scared of what might come up.

"It's about your exam. Well, your grade in particular. I'm afraid that you came up just one point shy of passing. I know how hard you have worked this year, and I just hate this. I mean, you came to tutoring, you were nice enough to stay after here today, you always do your homework; I know you have the right work ethic. Math just isn't your forte. But I would like to help you out." She finished with a friendly smile on her face.

Ash was stunned. He knew that he was not a good math student, but how could he fail! He felt sick. Why didn't he just study a little bit longer? Why didn't he go over his exam one more time? His mom was going to kill him for this! Before he ventured too far down the road of consequences, he remembered that Ms. Gray said she would like to help. Maybe there was hope after all.

"What exactly do you mean by that?" He asked, crossing his fingers.

"Well I was thinking I could give you some extra credit; enough so that you can pass this class."

Intense relief washed over Ash when he heard these words. He could pass after all. He had managed to get his teacher to like him enough for her to help him out. He hated her class, but he really liked Ms. Gray. She was extremely young for a teacher; she had to be in her twenties, and she was very nice and helpful. He had to admit; she was really attractive. He tried not to think about his own teacher like that, but he couldn't.

"What would I need to do for this extra credit?" A much calmer Ash asked.

"I haven't decided that just yet. I'm sure we could work something out." She finished with her soothing smile still present.

After chewing on her lip briefly, Ms. Gray got up from her desk and walked around to the same side of her desk that Ash was on. She was wearing a sleeveless, celeste top, a pair of long, black dress pants, and some short pump heels. Her long, luscious, blonde locks flowed smoothly down past her waist. She eyed Ash briefly, seemingly judging something about him, and nodded confirmation to herself after her contemplation.

She got out a piece of paper and reached for a pencil to start to write with it. She started writing a few words, and she spoke as she wrote them down.

"How about you help me out with- oops!" The pencil she was writing with managed to slip out of her grasp and rolled around on the ground.

She bent over to pick it up, purposely bending her back and knees in a way that her shirt would scoot up, and wiggled in a way to shimmy her pants down a little bit. She pretended to fumble around with the pencil, waving her slightly exposed ass in Ash's face. The only thing that gave her a little bit of coverage was some forest green underwear.

Once she thought she had stayed in her position for a sufficient time, she turned around and looked at Ash. His face was turning red, and he avoided her look. She smiled, knowing very well that he must have had a good luck at her. He, at this point, was obviously oblivious to her intentions. She glanced down at his lower body, and gained all the confirmation she needed.

"Yeah I think we can work something out right here and now," She stated in a softer voice as she rubbed her hand over his bulging erection.

"Wh-what do you mean?" Ash had lost his tranquility at this point.

"You're a smart man. I think you know what I mean." She responded.

Ash was almost too stunned to remove as what his math teacher was implying to him. He almost didn't realize what she was doing until he felt the pain that his suddenly too tight jeans had been causing ceased. He had been wearing a two-button orange polo, but he realized that it was no longer attached to his body. His raging erection was now only limited by his red boxers, but those, too, were soon lost.

"Ms. Gray! What are you doing?" Ash regained his ability to talk.

"Please, Ash, call me Cynthia." She responded as she licked her lips.

She gave no time for Ash to object, not that she expected him to; she was just impatient. She took his member in and started sucking on it. Ash had managed to convince himself that this was not a dream, and after overcoming the pure shock of the past minute, he succumbed to the pleasure that he was feeling.

"Oh Cynthia…" He softly cried out.

He had received a couple of blowjobs from his classmates before, but they paled in comparison to what he was getting now. Despite her young age for a teacher, she still had quite a few years on Ash, and would be considered a veteran in this field. Her wet mouth moved skillfully up and down his shaft, causing immense joy for Ash.

"Oh yes" He moaned as he continued to enjoy Cynthia's dirty work.

She looked up at him with her light brown eyes opened wide, aiming for an innocent façade, while she slowly took one, long lick over his full length. Just to change things up a bit, she moved down and pleasured his balls with her mouth. She sucked on both of them with her moist mouth, making Ash an even happier man.

"Oh my god, yes!" Ash now recognized that staying after today was his best decision of the school year.

Cynthia moved back to the main attraction, expertly finding a way to fit Ash inside of her with no problem. She seemed to have a fair amount of experience; she was adept with the use of her tongue. Every part of him was getting the gratification of having Cynthia bob her head up and down, repetitively.

"Cynthia!" Ash called her name as he knew he was getting close.

Cynthia made no flinch or acknowledgement that she heard, she just kept working on her task. Seconds later, Ash finished with a cry, and he sent his sperm spraying into her mouth. She swallowed it easily and eagerly; she even sucked on his tip some more to make sure that there weren't any leftovers. After she had gotten every last drop, Cynthia rose up off of her knees.

"What's it like to get sucked off by a real women?" She asked in a husky voice, taking a jab at the girls that Ash had alluded to earlier.

"Fucking amazing" He responded coolly.

Cynthia refused to wait any longer, and she yanked her pants off quickly. She took a little more time to be careful with her nice shirt; there was no need to ruin her clothes. Ash was only able to get a look at her matching underwear that was the color of leaves in the spring before her bra was discarded as well. Her C cup breasts popped out; her nipples were hard and perky.

"I haven't been with a man since I became a teacher. I need this." She claimed in a desperate voice that certified that she did need it.

Ash was still hard despite already releasing once, and he was ready to go. Cynthia bent over her desk, and slid her panties down to her ankles, where they hung just above her heels. She flipped her long hair off to the right side, and waited as patiently as she could for Ash to get started. Even though it was not a long wait, it seemed eternal to Cynthia. She was as wet as a pool down there and she was getting anxious.

Both of them released simultaneous gasps when Ash finally pushed inside of her wet entrance. Since Cynthia had gone so long without having sex, she was very tight. Her insides clamped down on the intruder, creating more bliss for Ash. Every nerve on his rod was sending back waves of pleasure due her walls squeezing him tightly.

"Oh I've never taken anyone this big before," Cynthia cooed.

It wasn't just a lie to boost Ash's self-esteem; she really hadn't ever taken anybody that big before. He wasn't some freak of nature that couldn't even fit, but he was big enough to stretch her out further than she ever had been. The long break that she had endured between her sexual interactions was all a part of a distant, unimportant past. None of that mattered; the wait was worth it.

"Deeper, Ash! Harder!" She demanded, wanting for her wonderful feelings to multiply.

Slightly surprised that she wanted to bump it up a level so quickly, Ash took a little bit to react to her wishes. However, he did not ignore them, and soon gave her what she wanted. He no longer gave timid, half pushes, and he started to get more intense. He now penetrated as deep as he could, making Cynthia give off powerful gasps.

"OH! Oh yes!" Even though she saw how long he was, she was still surprised at how far he managed to reach.

He penetrated to places that she had never had touched. She bit down on her lips and tongue to try and prevent herself from getting too loud. She was sure that most of administration was still on school grounds and if any of them ventured too close to where she was right not, her job would be in major jeopardy. Forget jeopardy. She would be fired on the spot.

"Mhm! Oh! Faster Ash, faster!" She pleaded out in a softer voice now that she had acknowledged what could happen if they were heard.

Ash smiled at this request, now he felt that he had the freedom to go all out if he pleased. He started to pump in at a much faster rate, multiplying his speed. He was still going all the way in, and each time he pushed to as deep as he could reach, a smacking noise was created. He felt in control of his teacher, a role swap that was interestingly enjoyable for Ash.

Cynthia, too, found herself enthralled by Ash's actions. Between the fact that she had gone so long without a man, and the fact that Ash was quite a man for his age, it was the best sex she had ever had. She knew that he was still an amateur at this, but he was catching on pretty quickly. With even more practice, he could be a golden catch for whoever ended up with him.

"Oh yeah! Just like that! Make me cum!" As great as this felt, she wanted to have her orgasm.

Ash understood that the end was near, and he gave it everything that he had. He pumped in and out of her a rigorous pace, roughly entering and exiting her over and over. He felt a few beads of sweat start to drop from his body, and just at that moment he realized how much energy he had been expending. He used his last reserve to make the final seconds as fantastic as possible.

"OHHH! OH! AH!" Cynthia screamed louder than she would have liked when she climaxed.

Ash pulled out hurriedly as he was coming to a close as well, but he didn't want to finish inside of her. Instead, he spun her around and dropped her down onto her knees, where he sprayed her with his second round of semen. Ash wished that he had a camera at this moment, because the sight of his beautiful geometry teacher with a face splashed with his cum was a sight he never wanted to forget.

They were both taking deep breaths to try and get some of their energy back. Cynthia closed her eyes and tried to relive what she had just gone through. It was the most physically pleasing moment that she could ever remember. She now knew that she had made the right decision in letting Ash gain his extra credit.

"I don't know Ash," She started, sounding unsure, "after what you just did, I kind of want to hold you back for another year."

"Oh don't worry," He responded, "I'll come back for some more tutoring."

* * *

**A/N: Not the best word and theme combination, but that is what happens when you get J. Sorry about the whole Ms. Gray thing, but I couldn't just have Ash call his teacher by her first name from the very beginning. So I searched for her last name on bulbapedia, and the first thing I saw on the info box was eye color: gray. So that's where I got gray XD.**

**The winner of last week's vote was Ash and the Sensational Sisters. I don't plan to include Misty, but that might change once I start to write it out. The options for chapter "L" are:**

**A. Gary and Misty B. Brock and Erika C. Ash and Melody D. Max and Molly (they will be older in the story than they are in the show/movie)**

**Thanks for reading!**


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